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(11) Patent Number: KE 309 (45) Date of grant: 31/03/2009
 
     Kenya Industrial Property Institute.

 
(19) Kenya Industrial Property Institute.
(12) PATENT
(51) Int.Cl.7: A 01N 43/56, 47/12, 47/18, 47/22, 47/24, 57/12, 57/14, 57/16, 57/20, 57/28
(21)Application    KE/P/ 2004/ 000374    (84) WO No. W02005/053406A1
Number:    16/06/2005
(22)Filing Date:    20/11/2004
(31)Priority Number: 102004021565.0 (32) Date: 03/05/2004 and 4/12/2003 (33) Country: and 10356549.3    DE 
(73) Owner(s): Bayer Cropscience Aktiengesellschaft of Afred-Nobel-Str 50, 40789 Monheim, Germany
(72) Inventor(s)    FISCHER, Reiner; FUNKE, Christian; HUNGENBERG,
Heike; ANDERSCH, Wolfram; THIELERT, Wolfgang; KRAUS, Anton and FISCHER, Rudiger
(74)Agent/address for correspondence: Kaplan & Stratton Advocates, P.O. Box 40111-00100,
Nairobi
(54) Title:    ACTIVE SUBSTANCE COMBINATIONS HAVING INSECTICIDAL
PROPERTIES.
(57) Abstract: The invention relates to novel insecticide combinations comprising anthranilic acid amides (group 1) and other insecticides selected among the group of (thio) phosphates (group 2) and/or the group of carbamates (group 3). Said insecticide combinations are very suitable for controlling animal pests such as insects.
 
-1-
Active substance combinations having insecticidal properties
The present invention relates to novel active compound combinations comprising, firstly, known anthranilamides and, secondly, further known insecticidally active compounds, which combinations 5    are highly suitable for controlling animal pests, such as insects.
It is already known that certain anthranilamides have insecticidal properties (WO 01/70671, WO 02/094791, WO 03/015519, WO 03/016284, WO 03/015518, WO 03/024222, WO 03/016282, WO 03/016283, WO 03/062226, WO 03/027099).
10
The generic formulae and definitions described in these publications, and the individual compounds described therein, are expressly incorporated herein by way of reference.
Furthermore, it is already known than numerous heterocycles, organotin compounds, benzoylureas
15 and pyrethroids have insecticidal and acaricidal properties (cf. WO 93/22297, WO 93/10083, DE-A 26 41 343, EP-A 347 488, EP-A 210 487, US 3,364,177 and EP-A 234 045). However, the activity of these compounds is likewise not always satisfactory.
It has now been found that mixtures of anthranilamides of the formula (1) (group 1) R3N,R2
20         (I)

in which
Al and A2 independently of one another represent oxygen or sulfur„
X1    represents N or atm,
R1    represents hydrogen or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-
25    cycloalkyl, each of which is optionally mono- or polysubstituted, where the substituents
independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4- alkylsulfonyl, C2-C4-alkoxycarbonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6- cycloalkylamino, (C1-C4-alkyl)-C3-C6-cycloalkylamino and R11,
 
-2-
R2    represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl,    C3-C6-cycloalkyl, C1-C4-
alkoxy,    C1-C4-alkylamino,    C2-C8-dialkylamino,    C3-C6-cycloalkylamino,    C2-C6-
alkoxycarbonyl or C2-C6-alkylcarbonyl,
R3    represents hydrogen, R1' or represents C1-C6-alkyl, C2-C6-alkenyl,    C3-C6-
 5 cycloalkyl, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl, RH, phenyl, phenoxy and a 5- or 6-membered heteroaromatic ring, where each phenyl, phenoxy
 10 and 5- or 6-membererd heteroaromatic ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12, or
R2 and R3 may be attached to one another and form the ring M,
R4    represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-
 15 haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, Ci-C4-alkylsulfinyl, C1-C4- allcylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl,
C2-C8-dialkylamino, C3-C6-cycloalkylamino, C3-C6-trialkylsilyl or represents phenyl, benzyl or phenoxy, each of which is optionally mono- or polysubstituted, where the
 20 substituents independently of one another may be selected from the group consisting of C1¬C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, CI-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, CI-C4alkoxy, Ci-C4- haloalkoxy, C1-C4-allcylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2- C8-dialkylamino, C3-C6-cycloalkylamino, C3-C6-(alkyl)cycloalkylamino, C2-C4-allcylcarbonyl,
 25 C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl, C3-C8-dialkylaminocarbonyl and C3-C6-trialkylsilyl,
R5 and R8 in each case independently of one another represent hydrogen, halogen or represent in each case optionally substituted C1-C4-alkyl, C1-C4-haloalkyl, R12, G, J, -0J, -OG, -S(0)p-J, -S(0)p¬G, -S(0)p-phenyl, where the substituents independently of one another may be selected from
 30 one to three radicals W or from the group consisting of R'2, C1-C10-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, C1-C4-alkoxy and C1-C4-alkythio, where each substituent may be substituted by one or more substituents independently of one another selected from the group consisting of G, J, R6, halogen, cyano, nitro, amino, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4- alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-
    35    haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-
trialkylsilyl, phenyl and phenoxy, where each phenyl or phenoxy ring may optionally be
 
-3-
substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
    G    in each case independently of one another represent a 5- or 6-membered non-aromatic
carbocyclic or heterocyclic ring which may optionally contain one or two ring members from
 5 the group consisting of C(=O), SO and S(=0)2 and which may optionally be substituted by one to four substituents independently of one another selected from the group consisting of C1-C2-alkyl, halogen, cyano, nitro and C1-C2-alkoxy, or independently of one another represent C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, (cyano)-C3-C7-cycloalkyl, (C1-C4¬alkyl)-C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-Ci-C4-alkyl, where each cycloalkyl,
    10    (alkyl)cycloalkyl and (cycloalkyl)alkyl may optionally be substituted by one or more halogen
atoms,
in each case independently of one another represent an optionally substituted 5- or 6-membered heteroaromatic ring, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
    15 R6    independently of one another represent -C(=E1)R19, -LC(=EI)R19, -C(=E1)LR19,
-LC(=E1)LR19, -0P(=Q)(0R19)2, -SO2LR18 or -LSO2LR19, where each E1 independently of one another represents 0, S,    N-OR15, N-N(R15)2,    N-CN or N-NO2,
    R7    represents hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy,
C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio,
    20    haloalkylsulfinyl, C1-C4-haloalkylsulfonyl,
    R9    represents C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylsulfinyl or halogen,
    R1°    represents hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, halogen, cyano or C1-C4-haloalkoxy,
    R11    in each case independently of one another represents in each case optionally mono- to
trisubstituted    Cl-C6-alkylthio,    C1-C6-alkylsulfenyl,    C1-C6-haloalkythio,    Ci-C6-
    25    haloalkylsulfenyl, phenylthio or phenylsulfenyl, where the substituents independently of one
another may be selected from the list W, -S(0).N(R16)2, -q=0)R13,
-S(C=0)LR14,C(=0)1a13,    -S(0),NR13C(=O)R13,    _s(0)nNit 13 C(=0)LR14    or
-S(0),INR13S(0)2LR14,
L    in each case independently of one another represents 0, NR18 or S,
    30 R12    in each case independently of one another represents -B(ORI7)2, amino, SH, thiocyanato, C3-
C8-trialkylsilyloxy, C1-C4-alkyl disulfide, -SF5, -C(=E)R19, -LC(=E)R19, -C(=E)LR19, -LC(=E)LR19, -0P(=Q)(0R19)2, -SO2LR19 or -L5O2LR19,
    Q    represents 0 or S,
    R13    in each case independently of one another represent hydrogen or represent in each case
    35    optionally mono- or polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-
cycloalkyl, where the substituents independently of one another may be selected from the
 
-4-
group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino or (C1- C4-alkyl)-C3-C6-cycloallcylamino,
R14    in each case independently of one another represent in each case optionally mono- or
5    polysubstituted C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl or C3-C6-cycloalkyl, where the
substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylsulfmyl, C1-C4-alkylsulfonyl, C1- C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino and (C1-C4-alkyD-C3-C6- cycloalkylamino or represent optionally substituted phenyl, where the substituents
10        independently of one another may be selected from one to three radicals W or one or more
radicals R12,
R15    in each case independently of one another represent hydrogen or represent in each case
optionally mono- or polysubstituted C1-C6-haloalkyl or C1-C6-alkyl, where the substituents
independently of one another may be selected from the group consisting of cyano, nitro,
15 hydroxyl, C1-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4- allcylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4- alkylamino, C2-C8-dialkylamino, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6- trialkylsily1 and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals 1112, or N(R15)2
20    represents a cycle which forms the ring M,
R16    represents C1-C12-alkyl or C1-C12-haloalkyl, or N(R16)2 represents a cycle which forms the
ring M,
R17    in each case independently of one another represent hydrogen or C1-C4-alkyl, or B(OR1)2
represents a ring in which the two oxygen atoms are attached via a chain having two to three 25    carbon atoms which are optionally substituted by one or two substituents independently of
one another selected from the group consisting of methyl and C2-C6-alkoxycarbonyl,
R18        in each case independently of one another represent hydrogen, C1-C6-alkyl or C1-C6-
haloalkyl, or N(R13)(R18) represents a cycle which forms the ring M,
1119    in each case independently of one another represent hydrogen or represent in each case
30    mono- or polysubstituted C1-C6-alkyl, where the substituents independently of one another
may be selected from the group consisting of cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4- haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfmyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, CO2H, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsily1 and optionally
35    substituted phenyl, where the substituents independently of one another may be selected from
 
-5-
one to three radicals W, C1-C6-haloalkyl, C3-C6-cycloalkyl or phenyl or pyridyl, each of which is optionally mono- to trisubstituted by W,
in each case represents an optionally mono- to tetrasubstituted ring which, in addition to the
nitrogen atom attached to the substituent pair R13 and R18, (R15)2 or (R16)2, contains two to six
5 carbon atoms and optionally additionally a further nitrogen, sulfur or oxygen atom, where the substituents independently of one another may be selected from the group consisting of C1¬C2-alkyl, halogen, cyano, nitro and Ci-C2-alkoxy,
W    in each case independently of one another represent C1-C4-alkyl, C2-C4-alkenyl, C2-C4-
alkynyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-
10 halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, Ci¬C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6- cycloalkylamino, (C1-C4-alkyl)-C3-C6-cycloallcylamino, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, CO2H, C2-C6-alkylaminocarbonyl, C3-C8-dialkylaminocarbonyl or C3-C6- trialkylsilyl,
15 n    in each case independently of one another represent 0 or 1,
p    in each case independently of one another represent 0, 1 or 2,
where, if (a) R5 represents hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-
haloalkynyl, C1-C4-haloalkoxy, Cr-C4-haloalkylthio or halogen and (b) R8 represents hydrogen, C1-C6-
20 alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio, halogen, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl, (c) at least one substituent selected from the group consisting of R6, R11 and R12 is present and (d) if R.12 is not present, at least one of the radicals R6 and R11 is different from C2- C6-alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6-alkylaminocarbonyl and C3-C8-dialkylaminocarbonyl,
25 and
where the compound of the general formula (I) may also be an N-oxide or salt,
and at least one insecticidally active compound of groups 2 and 3 below selected from 30 A)    (thio)phosphates (group 2), preferably
(2-1) azinphos-methyl (known from US 2,758,115)
 
and/or
(2-2) chlorpyrifos (known from US 3,244,586)
 
-6-
S
H5C2011,0    CI
H5c20
and/or
(2-3) diazinon (known from US 2,754,243) H3C
)=-N
(H3C)2CH
 
5    and/or
(2-4) dimethoate (known from US 2,494,283)
0
II    II
H3C-N-C-CHFS-1-0CH3
H    OCH3
and/or
(2-5) disulfoton (known from DE-A 91 76 68)
1-15C20,1j/SN/'\ s CH3
10    OC2H5
and/or
(2-6) ethion (known from US 2,873,228)
H5C20,1:1,,S.,,s, IF!, 002H,
0C2H5    0C2H5
and/or
15    (2-7) fenitrothion (known from BE-A 0 594 669)
S „00H,
02N    oi 'OCH3
H3C
and/or
(2-8) fenthion (known from DE-A 11 16656)
SCH3
H3C0-1■0
H3C0
20    and/or
(2-9) isoxathion (known from DE-A 15 67 137)
 
N-0
 

 
and/or
(2-10) malathion (known from US 2,578,562) 0
s
OCH3 ,    0
0 0C2H5
    5    and/or
(2-11) methidathion (known from DE-A 16 45 982)
OCH3
N
    I    s
OCH3    11110
and/or
(2-12) oxydemeton-methyl (known from DE-A 94 73 68)
0
C2
H,
H3C0—p's/N, 0
H3CO
and/or
(2-13) parathion (known from DE-A 81 41 52) H,C20\ s
H5C20 0    NO2
and/or
    15    (2-14) parathion-methyl (known from DE-A 81 41 42)
H3CON
H3C0/ "0    NO2
and/or
(2-15) phenthoate (lmown from GB-A 834 814)
Y    II
C-S—P—OCH3
„CN OCH3
0C2H5
    20    and/or
 
-8-
(2-16) phorate (known from US 2,586,655)
(1)02H,
H5C2S—s_r _oc2H5
S
and/or
(2-17) phosalone (known from DE-A 24 31 192)
S
I I
HSO20-7—S-1
H,C20
O
0 v CI
and/or
(2-18) phosmet (known from US 2,767,194)
 

 
and/or
10    (2-19) phoxim (known from DE-A 12 38 902)
    IIS
 H,C20—P— 0
0C21-15     
and/or        CN

(2-20) pirimiphos-methyl (known from DE-A 14 45 949)
H3CO3\1■,„0
H3CO         CH3
H5CcNNC2H5
15    and/or
 
(2-21) profenophos (known from DE-A 22 49 462)
S,011 0
H3C
H,C20
CI
and/or
(2-22) prothiophos (known from DE-A 21 11 414)
 
°
H5C20
CI         -9-
CI

and/or
(2-23) tebupirimphos (known from DE-A 33 17 824) H5C20,
FI,C
).--0 0
H3C
and/or
(2-26) dichlotphos (known from GB-A 775 085)
    0    CI
I ICI
OCH3
and/or
15    (2-27) dicrotophos (known from BE-A 55 22 84)
    0    H TH3
    H3CO3\%    N
CH,
    H3C0    CH3
and/or
(2-28) mevinphos (known from US 2,685,552) H3C0 /O
P-0    CO2CH3
H3C0
H3C
20    and/or
(2-29) monocrotophos (known from DE-A 19 64 535)
 
- 10 -
H3CRI?    CH3
P-0
H3CO
H3C
and/or
(2-30) phosphamidon (known from US 2,908,605) H3CRRO    /C21-15
P-0
H3C    Nis
H3C    CI
5    and/or
(2-31) acephate (known from DE-A 20 14 027) 0
H3C—S,Id,N,f0
OCH3 CH3
and/or
(2-32) methamidophos (known from US 3,309,266) 0
H3C—S,1 I„NH2
OCH3
and/or
(2-33) trichlorfon (known from US 2,701,225)
0 TC13
,C.
,P OH
H3C0
OCH3
and/or
B)    carbamates (group 3), preferably
(3-1) carbaryl (known from US 2,903,478)
0 I I
0—C—N—CH3
 
and/or
20    (3-2) fenoxycarb (known from EP-A 0 004 334)
0
 
and/or
(3-3) formetanate (known from DE-A 11 69 194)
CH3 =C—N
0 I    D H CH3
H3C—N—C-0
HI
and/or
(3-4) formetanate hydrochloride (known from DE-A 11 69 194) and/or
(3-5) methiocarb (known from DE-A 11 62 352)
H
,N 0    CH3
H3C
SCH3
CH3
and/or
10    (3-6) methomyl (known from US 3,639,620)
0
H3c, .,
SUCH3
CH3
and/or
(3-7) oxamyl (known from DE-A 17 68 623)
0    0
H,C,N    N/CH3
SCH3 CH3
15    and/or
(3-8) pirimicarb (= Pirimor) (known from GB-A 1 181 657)
CH3    ?F13
H3C    0 N,
cH3
N``/    0
,
H3CN, CH3
and/or
(3-9) propoxur (known from DE-A 11 08 202)
 
and/or
(3-10) thiodicarb (known from DE-A 25 30 439)
CH3    0    0    CHs
I
S    `O    A ,..N S
'1%-ON`y
I    I
CH3    CH3 CH3    CH3
5
are synergistically effective and suitable for controlling animal pests.
Surprisingly, the insecticidal and acaricidal activity of the active compound combination according to the invention is considerably higher than the sum of the activities of the individual active compounds. 10    An unforeseeable true synergistic effect is present, and not just an addition of activities.
In addition to at least one active compound of the formula (1), the active compound combinations according to the invention comprise at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or group 3 [selected from the compounds (3-1) to (3-10)].
15
Depending inter alia on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of varying composition which, if appropriate, can be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their preparation and use and compositions comprising them.
20 However, hereinbelow, for the sake of simplicity, only compounds of the formula (1) are referred to, although what is meant are both the pure compounds and, if appropriate, also mixtures having varying proportions of isomeric compounds.
Preference is given to active compound combinations comprising compounds of the formula (1-1)
25     
    in which
R2    represents hydrogen or C1-C6-alkyl,
 
- 13 -
    R3    represents C1-C6-alkyl which is optionally substituted by one R6,
    R4    represents C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or halogen,
    R5    represents hydrogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or halogen,
    R6    represents -C(=E2)R19, -LC(=E2)R19, -C(=E2)LR19 or -LC(=E2)LR19, where each E2
5        independently of one another represents 0, S, N-R15, N-OR15, N-N(R15)2, and each L
independently of one another represents 0 or NR18,
    R7    represents C1-C4-haloalkyl or halogen,
    R9    represents C1-C2-haloalkyl, C1-C2-haloalkoxy, S(0)p-C1-C2-haloallcyl or halogen,
    R15    in each case independently of one another represent hydrogen or represent in each case
10 optionally substituted C1-C6-haloalkyl or Cl-C6-alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, C1-C4-alkoxy, C1-C4- haloalkoxy, C1-C4-alkylthio, CI-C4alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloallcylsulfmyl and C1-C4-haloalkylsulfonyl,
    R'8    in each case represents hydrogen or Ci-C4-alkyl,
    15 R19    in each case independently of one another represent hydrogen or C1-C6-alkyl,
p    independently of one another represent 0, 1, 2,
and at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or of group 3 [selected from the compounds (3-1) to (3-10)].
20 In the radical definitions mentioned as being preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
Particular preference is given to active compound combinations comprising compounds of the formula (I-1) in which
    25 R2    represents hydrogen or methyl,
    R3    represents C1-C4-alkyl (in particular methyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl),
    R4    represents methyl, trifluoromethyl, trifluoromethoxy, fluorine, chlorine, bromine or iodine,
    R5    represents hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl or trifluoromethoxy,
    R7    represents chlorine or bromine,
    30 R9    represents trifluoromethyl, chlorine, bromine, difluoromethoxy or trifluoroethoxy,
and at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or of group 3 [selected from the compounds (3-1) to (3-10)].
Very particular preference is given to active compound combinations comprising the following 35 compounds of the formula (I-1):
 
- 14 -
 

Example    R2    R3    R4    R5    R7    R9    m.p. (°C)
No.                           
I-1-1    H    Me    Me    Cl    Cl    CF3    185-186
1-1-2    H    Me    Me    Cl    Cl    OCH2CF3    207-208
1-1-3    H    Me    Me    Cl    Cl    Cl    225-226
1-1-4    H    Me    Me    Cl    Cl    Br    162-164
1-1-5    H    Me    Cl    Cl    Cl    CF3    155-157
1-1-6    H    Me    Cl    Cl    Cl    OCH2CF3    192-195
1-1-7    H    Me    Cl    Cl    Cl    Cl    205-206
1-1-8    H    Me    Cl    Cl    Cl    Br    245-246
1-1-9    H    i-Pr    Me    Cl    Cl    CF3    195-196
1-1-10    H    i-Pr    Me    Cl    Cl    OCH2CF3    217-218
1-1-11    H    i-Pr    Me    Cl    Cl    Cl    173-175
1-1-12    H    i-Pr    Me    Cl    Cl    Br    159-161
1-1-13    H    i-Pr    Cl    Cl    Cl    CF3    200-201
1-1-14    H    i-Pr    Cl    Cl    Cl    OCH2CF3    232-235
1-1-15    H    i-Pr    Cl    Cl    Cl    Cl    197-199
1-1-16    H    i-Pr    Cl    Cl    Cl    Br    188-190
1-1-17    H    Et    Me    Cl    Cl    CF3    163-164
1-1-18    H    Et    Me    Cl    Cl    OCH2CF3    205-207
1-1-19    H    Et    Me    Cl    Cl    Cl    199-200
1-1-20    H    Et    Me    Cl    Cl    Br    194-195
1-1-21    H    Et    Cl    Cl    Cl    CF3    201-202
1-1-22    H    Et    Cl    Cl    Cl    Cl    206-208
1-1-23    H    Et    Cl    Cl    Cl    Br    214-215
1-1-24    H    t-Bu    Me    Cl    Cl    CF3    223-225
1-1-25    H    t-Bu    Me    Cl    Cl    Cl    163-165
1-1-26    H    t-Bu    Me    Cl    Cl    Br    159-161
1-1-27    H    t-Bu    Cl    Cl    Cl    CF3    170-172
1-1-28    H    t-Bu    Cl    Cl    Cl    Cl    172-173
1-1-29    H    t-Bu    Cl    Cl    Cl    Br    179-180
1-1-30    H    Me    Me    Br    Cl    CF3    222-223
1-1-31    H    Et    Me    Br    Cl    CF3    192-193
1-1-32    H    i-Pr    Me    Br    Cl    CF3    197-198
1-1-33    H    t-Bu    Me    Br    Cl    CF3    247-248
1-1-34    H    Me    Me    Br    Cl    Cl    140-141
1-1-35    H    Et    Me    Br    Cl    Cl    192-194
 
- 15 -

Example    R2    R3    R4    R5    R7    R9    m.p. (°C)
No.                           
1-1-36    H    i-Pr    Me    Br    Cl    Cl    152-153
I-1-37    H    t-Bu    Me    Br    Cl    Cl    224-225
1-1-38    H    Me    Me    Br    Cl    Br    147-149
1-1-39    H    Et    Me    Br    Cl    Br    194-196
1-1-40    H    i-Pr    Me    Br    Cl    Br    185-187
I-1-41    H    t-Bu    Me    Br    CI    Br    215-221
1-1-42    H    Me    Me    I    CI    CF3    199-200
1-1-43    H    Et    Me    I    CI    CF3    199-200
1-1-44    H    i-Pr    Me    I    Cl    CF3    188-189
I-1-45    H    t-Bu    Me    I    Cl    CF3    242-243
1-1-46    H    Me    Me    I    Cl    Cl    233-234
1-1-47    H    Et    Me    I    Cl    Cl    196-197
1-1-48    H    i-Pr    Me    I    Cl    Cl    189-190
1-1-49    H    t-Bu    Me    I    Cl    Cl    228-229
I-1-50    H    Me    Me    I    Cl    Br    229-230
1-1-51    H    iPr    Me    I    Cl    Br    191-192
1-1-52    H    Me    Br    Br    Cl    CF3    162-163
1-1-53    H    Et    Br    Br    Cl    CF3    188-189
1-1-54    H    i-Pr    Br    Br    Cl    CF3    192-193
I-1-55    H    t-Bu    Br    Br    Cl    CF3    246-247
I-1-56    H    Me    Br    Br    Cl    Cl    188-190
1-1-57    H    Et    Br    Br    Cl    Cl    192-194
1-1-58    H    i-Pr    Br    Br    Cl    Cl    197-199
1-1-59    H    t-Bu    Br    Br    Cl    Cl    210-212
1-1-60    H    Me    Br    Br    Cl    Br    166-168
1-1-61    H    Et    Br    Br    Cl    Br    196-197
1-1-62    H    i-Pr    Br    Br    Cl    Br    162-163
1-1-63    H    t-Bu    Br    Br    Cl    Br    194-196
1-1-64    H    t-Bu    Cl    Br    Cl    CF3    143-145
1-1-65    Me    Me    Br    Br    Cl    Cl    153-155
1-1-66    Me    Me    Me    Br    Cl    CF3    207-208
1-1-67    Me    Me    Cl    Cl    Cl    Cl    231-232
1-1-68    Me    Me    Br    Br    Cl    Br    189-190
1-1-69    Me    Me    Cl    Cl    Cl    Br    216-218
1-1-70    Me    Me    Cl    Cl    Cl    CF3    225-227
1-1-71    Me    Me    Br    Br    Cl    CF3    228-229
1-1-72    H    i-Pr    Me    H    Cl    CF3    237-239

and at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or of group 3 [selected from the compounds (3-1) to (3-10)].
 

 

 

 

 
-20-
 

 
H3
 

 
CF3    CF3
    (I-1-71)    (1-1-72)
5 and at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or of group 3 [selected from the compounds (3-1) to (3-10)].
Preference is given to active compound combinations which preferably comprise the following active compounds of group 2:
10    (2-2) chlorpyrifos,
(2-31) acephate,
(2-32) methamidophos.
Preference is given to active compound combinations according to the invention which preferably 15 comprise the following active compounds of group 3:
(3-1) carbaryl,
(3-5) methiocarb,
(3-10) thiodicarb.
20 Emphasis is given to the following specifically mentioned active compound combinations (2-component mixtures) comprising a compound of the formula (I-1) and the stated active compound of group 2 or of group 3:
 
-21 -
No    Active compound combination
comprising    No .    Active compound combination
comprising
la)    (I-1-1) and (2-2) chlorpyrifos    28a)    (1-1-39) and (2-2) chlorpyrifos
lb)    (I-1-1) and (2-31) acephate    28b)    (1-1-39) and (2-31) acephate
lc)    (I-1-1) and (2-32) methamidophos    28c)    (I-1-39) and (2-32) methamidophos
1d)    (I-1-1) and (3-1) carbaryl    28d)    (1-1-39) and (3-1) carbaryl
1e)    (I-1-1) and (3-5) methiocarb    28e)    (I-1-39) and (3-5) methiocarb
if)    (I-1-1) and (3-10) thiodicarb    28f)    (I-1-39) and (3-10) thiodicarb
2a)    (I-1-2) and (2-2) chlorpyrifos    29a)    (1-1-40) and (2-2) chlorpyrifos
2b)    (I-1-2) and (2-31) acephate    29b)    (I-1-40) and (2-31) acephate
2c)    (1-1-2) and (2-32) methamidophos    29c)    (1-1-40) and (2-32) methamidophos
2d)    (I-1-2) and (3-1) carbaryl    29d)    (I-1-40) and (3-1) carbaryl
2e)    (I-1-2) and (3-5) methiocarb    29e)    (I-1-40) and (3-5) methiocarb
2f)    (1-1-2) and (3-10) thiodicarb    29f)    (I-1-40) and (3-10) thiodicarb
3a)    (I-1-3) and (2-2) chlorpyrifos    30a)    (I-1-42) and (2-2) chlorpyrifos
3b)    (I-1-3) and (2-31) acephate    30b)    (I-1-42) and (2-31) acephate
3c)    (I-1-3) and (2-32) methamidophos    30c)    (1-1-42) and (2-32) methamidophos
3d)    (I-1-3) and (3-1) carbaryl    30d)    (I-1-42) and (3-1) carbaryl
3e)    (I-1-3) and (3-5) methiocarb    30e)    (I-1-42) and (3-5) methiocarb
3f)    (I-1-3) and (3-10) thiodicarb    301)    (I-1-42) and (3-10) thiodicarb
4a)    (1-1-4) and (2-2) chlorpyrifos    31a)    (1-1-43) and (2-2) chlorpyrifos
4b)    (I-1-4) and (2-31) acephate    31b)    (I-1-43) and (2-31) acephate
4c)    (1-1-4) and (2-32) methamidophos    31c)    (1-1-43) and (2-32) methamidophos
4d)    (1-1-4) and (3-1) carbaryl    31d)    (I-1-43) and (3-1) carbaryl
4e)    (1-1-4) and (3-5) methiocarb    31e)    (1-1-43) and (3-5) methiocarb
4f)    (I-1-4) and (3-10) thiodicarb    31f)    (1-1-43) and (3-10) thiodicarb
5a)    (I-1-5) and (2-2) chlorpyrifos    32a)    (I-1-44) and (2-2) chlorpyrifos
5b)    (1-1-5) and (2-31) acephate    32b)    (I-1-44) and (2-31) acephate
5c)    (I-1-5) and (2-32) methamidophos    32c)    (I-1-44) and (2-32) methamidophos
5d)    (I-1-5) and (3-1) carbaryl    32d)    (1-1-44) and (3-1) carbaryl
5e)    (I-1-5) and (3-5) methiocarb    32e)    (I-1-44) and (3-5) methiocarb
5f)    (I-1-5) and (3-10) thiodicarb    32f)    (I-1-44) and (3-10) thiodicarb
6a)    (1-1-6) and (2-2) chlorpyrifos    33a)    (1-1-50) and (2-2) chlorpyrifos
6b)    (I-1-6) and (2-31) acephate    33b)    (I-1-50) and (2-31) acephate
6c)    (1-1-6) and (2-32) methamidophos    33c)    (1-1-50) and (2-32) methamidophos
6d)    (1-1-6) and (3-1) carbaryl    33d)    (I-1-50) and (3-1) carbaryl
6e)    (1-1-6) and (3-5) methiocarb    33e)    (1-1-50) and (3-5) methiocarb
6f)    (I-1-6) and (3-10) thiodicarb    33f)    (1-1-50) and (3-10) thiodicarb
7a)    (1-1-7) and (2-2) chlorpyrifos    34a)    (1-1-51) and (2-2) chlorpyrifos
7b)    (1-1-7) and (2-31) acephate    34b)    (I-1-51) and (2-31) acephate
7c)    (I-1-7) and (2-32) methamidophos    34c)    (I-1-51) and (2-32) methamidophos
 
- 22 -
No    Active compound combination
comprising    No .    Active compound combination
comprising
7d)    (I-1-7) and (3-1) carbaryl    34d)    (1-1-51) and (3-1) carbaryl
7e)    (1-1-7) and (3-5) methiocarb    34e)    (1-1-51) and (3-5) methiocarb
7f)    (I-1-7) and (3-10) thiodicarb    34f)    (I-1-51) and (3-10) thiodicarb
8a)    (I-1-8) and (2-2) chlorpyrifos    35a)    (I-1-52) and (2-2) chlorpyrifos
8b)    (I-1-8) and (2-31) acephate    35b)    (I-1-52) and (2-31) acephate
8c)    (I-1-8) and (2-32) methamidophos    35c)    (I-1-52) and (2-32) methamidophos
8d)    (1-1-8) and (3-1) carbaryl    35d)    (1-1-52) and (3-1) carbaryl
8e)    (1-1-8) and (3-5) methiocarb    35e)    (I-1-52) and (3-5) methiocarb
8f)    (I-1-8) and (3-10) thiodicarb    351)    (I-1-52) and (3-10) thiodicarb
9a)    (1-1-9) and (2-2) chlorpyrifos    36a)    (I-1-53) and (2-2) chlorpyrifos
9b)    (I-1-9) and (2-31) acephate    36b)    (1-1-53) and (2-31) acephate
9c)    (1-1-9) and (2-32) methamidophos    36c)    (1-1-53) and (2-32) methamidophos
9d)    (1-1-9) and (3-1) carbaryl    36d)    (I-1-53) and (3-1) carbaryl
9e)    (1-1-9) and (3-5) methiocarb    36e)    (1-1-53) and (3-5) methiocarb
9f)    (1-1-9) and (3-10) thiodicarb    360    (1-1-53) and (3-10) thiodicarb
10a)    (1-1-11) and (2-2) chlorpyrifos    37a)    (1-1-54) and (2-2) chlorpyrifos
10b)    (I-1-11) and (2-31) acephate    37b)    (1-1-54) and (2-31) acephate
10c)    (I-1-11) and (2-32) methamidophos    37c)    (I-1-54) and (2-32) methamidophos
10d)    (I-1-11) and (3-1) carbaryl    37d)    (I-1-54) and (3-1) carbaryl
10e)    (I-1-11) and (3-5) methiocarb    37e)    (I-1-54) and (3-5) methiocarb
100    (1-1-11) and (3-10) thiodicarb    370    (I-1-54) and (3-10) thiodicarb
11 a)    (I-1-12) and (2-2) chlorpyrifos    38a)    (1-1-55) and (2-2) chlorpyrifos
11b)    (1-1-12) and (2-31) acephate    38b)    (I-1-55) and (2-31) acephate
11c)    (1-1-12) and (2-32) methamidophos    38c)    (1-1-55) and (2-32) methamidophos
lid)    (I-1-12) and (3-1) carbaryl    38d)    (I-1-55) and (3-1) carbaryl
11 e)    (I-1-12) and (3-5) methiocarb    38e)    (1-1-55) and (3-5) methiocarb
110    (I-1-12) and (3-10) thiodicarb    38f)    (I-1-55) and (3-10) thiodicarb
12a)    (I-1-13) and (2-2) chlorpyrifos    39a)    (I-1-56) and (2-2) chlorpyrifos
12b)    (1-1-13) and (2-31) acephate    39b)    (I-1-56) and (2-31) acephate
12c)    (1-1-13) and (2-32) methamidophos    39c)    (I-1-56) and (2-32) methamidophos
12d)    (1-1-13) and (3-1) carbaryl    39d)    (1-1-56) and (3-1) carbaryl
12e)    (I-1-13) and (3-5) methiocarb    39e)        (1-1-56) and (3-5) methiocarb
120    (1-1-13) and (3-10) thiodicarb    39f)        (1-1-56) and (3-10) thiodicarb
13a)    (I-1-15) and (2-2) chlorpyrifos    40a)    (1-1-57) and (2-2) chlorpyrifos
13b)    (I-1-15) and (2-31) acephate    40b)    (I-1-57) and (2-31) acephate
13c)    (1-1-15) and (2-32) methamidophos    40c)    (I-1-57) and (2-32) methamidophos
13d)    (I-1-15) and (3-1) carbaryl    40d)    (I-1-57) and (3-1) carbaryl
13e)    (I-1-15) and (3-5) methiocarb    40e)    (I-1-57) and (3-5) methiocarb
 
- 23 -
No    Active compound combination
comprising    No .    Active compound combination
comprising
130    (I-1-15) and (3-10) thiodicarb    40f)    (I-1-57) and (3-10) thiodicarb
14a)    (I-1-16) and (2-2) chlorpyrifos    41a)    (I-1-58) and (2-2) chlorpyrifos
14b)    (I-1-16) and (2-31) acephate    41b)    (I-1-58) and (2-31) acephate
14c)    (I-1-16) and (2-32) methamidophos    41c)    (I-1-58) and (2-32) methamidophos
14d)    (I-1-16) and (3-1) carbaryl    41d)    (1-1-58) and (3-1) carbaryl
14e)    (I-1-16) and (3-5) methiocarb    41e)    (I-1-58) and (3-5) methiocarb
140    (I-1-16) and (3-10) thiodicarb    410    (I-1-58) and (3-10) thiodicarb
15a)    (1-1-19) and (2-2) chlorpyrifos    42a)    (I-1-60) and (2-2) chlorpyrifos
15b)    (I-1-19) and (2-31) acephate    42b)    (I-1-60) and (2-31) acephate
15c)    (1-1-19) and (2-32) methamidophos    42c)    (1-1-60) and (2-32) methamidophos
15d)    (I-1-19) and (3-1) carbaryl    42d)    (1-1-60) and (3-1) carbaryl
15e)    (I-1-19) and (3-5) methiocarb    42e)    (I-1-60) and (3-5) methiocarb
151)    (1-1-19) and (3-10) thiodicarb    420    (I-1-60) and (3-10) thiodicarb
16a)    (1-1-21) and (2-2) chlorpyrifos    43a)    (I-1-61) and (2-2) chlorpyrifos
16b)    (I-1-21) and (2-31) acephate    43b)    (1-1-61) and (2-31) acephate
16c)    (I-1-21) and (2-32) methamidophos    43c)    (I-1-61) and (2-32) methamidophos
16d)    (1-1-21) and (3-1) carbaryl    43d)    (1-1-61) and (3-1) carbaryl
16e)    (I-1-21) and (3-5) methiocarb    43e)    (1-1-61) and (3-5) methiocarb
160    (1-1-21) and (3-10) thiodicarb    431)    (1-1-61) and (3-10) thiodicarb
17a)    (I-1-22) and (2-2) chlorpyrifos    44a)    (I-1-62) and (2-2) chlorpyrifos
17b)    (1-1-22) and (2-31) acephate    44b)    (1-1-62) and (2-31) acephate
17c)    (I-1-22) and (2-32) methamidophos    44c)    (I-1-62) and (2-32) methamidophos
17d)    (I-1-22) and (3-1) carbaryl    44d)    (1-1-62) and (3-1) carbaryl
17e)    (1-1-22) and (3-5) methiocarb    44e)    (1-1-62) and (3-5) methiocarb
171)    (1-1-22) and (3-10) thiodicarb    440    (1-1-62) and (3-10) thiodicarb
18a)    (I-1-23) and (2-2) chlorpyrifos    45a)    (I-1-64) and (2-2) chlorpyrifos
18b)    (I-1-23) and (2-31) acephate    45b)    (I-1-64) and (2-31) acephate
18c)    (1-1-23) and (2-32) methamidophos    45c)    (I-1-64) and (2-32) methamidophos
18d)    (1-1-23) and (3-1) carbaryl    45d)    (1-1-64) and (3-1) carbaryl
18e)    (1-1-23) and (3-5) methiocarb    45e)    (1-1-64) and (3-5) methiocarb
180    (1-1-23) and (3-10) thiodicarb    450    (1-1-64) and (3-10) thiodicarb
19a)    (I-1-24) and (2-2) chlorpyrifos    46a)    (I-1-65) and (2-2) chlorpyrifos
19b)    (1-1-24) and (2-31) acephate    46b)    (I-1-65) and (2-31) acephate
19c)    (1-1-24) and (2-32) methamidophos    46c)    (1-1-65) and (2-32) methamidophos
19d)    (1-1-24) and (3-1) carbaryl    46d)    (1-1-65) and (3-1) carbaryl
19e)    (1-1-24) and (3-5) methiocarb    46e)    (I-1-65) and (3-5) methiocarb
190    (1-1-24) and (3-10) thiodicarb    460    (1-1-65) and (3-10) thiodicarb
20a)    (I-1-26) and (2-2) chlorpyrifos    47a)    (I-1-66) and (2-2) chlorpyrifos
 
- 24 -
No    Active compound combination
comprising    No .    Active compound combination
comprising
20b)    (1-1-26) and (2-31) acephate    47b)    (I-1-66) and (2-31) acephate
20c)    (I-1-26) and (2-32) methamidophos    47c)    (1-1-66) and (2-32) methamidophos
20d)    (I-1-26) and (3-1) carbaryl    47d)    (1-1-66) and (3-1) carbaryl
20e)    (I-1-26) and (3-5) methiocarb    47e)    (I-1-66) and (3-5) methiocarb
20f)    (1-1-26) and (3-10) thiodicarb    47f)    (I-1-66) and (3-10) thiodicarb
21a)    (1-1-27) and (2-2) chlorpyrifos    48a)    (I-1-67) and (2-2) chlorpyrifos
21b)    (1-1-27) and (2-31) acephate    48b)    (1-1-67) and (2-31) acephate
21c)    (I-1-27) and (2-32) methamidophos    48c)    (1-1-67) and (2-32) methamidophos
21d)    (I-1-27) and (3-1) carbaryl    48d)    (1-1-67) and (3-1) carbaryl
21e)    (I-1-27) and (3-5) methiocarb    48e)        (I-1-67) and (3-5) methiocarb
210    (I-1-27) and (3-10) thiodicarb    48f)        (I-1-67) and (3-10) thiodicarb
22a)    (I-1-29) and (2-2) chlorpyrifos    49a)    (I-1-68) and (2-2) chlorpyrifos
22b)    (I-1-29) and (2-31) acephate    49b)    (I-1-68) and (2-31) acephate
22c)    (I-1-29) and (2-32) methamidophos    49c)    (1-1-68) and (2-32) methamidophos
22d)    (I-1-29) and (3-1) carbaryl    49d)    (I-1-68) and (3-1) carbaryl
22e)    (1-1-29) and (3-5) methiocarb    49e)    (I-1-68) and (3-5) methiocarb
22f)    (I-1-29) and (3-10) thiodicarb    49f)    (I-1-68) and (3-10) thiodicarb
23a)    (I-1-30) and (2-2) chlorpyrifos    50a)    (I-1-69) and (2-2) chlorpyrifos
23b)    (I-1-30) and (2-31) acephate    50b)    (I-1-69) and (2-31) acephate
23c)    (I-1-30) and (2-32) methamidophos    50c)    (I-1-69) and (2-32) methamidophos
23d)    (I-1-30) and (3-1) carbaryl    50d)    (I-1-69) and (3-1) carbaryl
23e)    (1-1-30) and (3-5) methiocarb    50e)    (I-1-69) and (3-5) methiocarb
23f)    (I-1-30) and (3-10) thiodicarb    500    (1-1-69) and (3-10) thiodicarb
24a)    (I-1-31) and (2-2) chlorpyrifos    51a)    (I-1-70) and (2-2) chlorpyrifos
24b)    (I-1-31) and (2-31) acephate    51b)    (I-1-70) and (2-31) acephate
24c)    (I-1-31) and (2-32) methamidophos    51c)    (I-1-70) and (2-32) methamidophos
24d)    (I-1-31) and (3-1) carbaryl    51d)    (I-1-70) and (3-1) carbaryl
24e)    (I-1-31) and (3-5) methiocarb    51e)    (I-1-70) and (3-5) methiocarb
24f)    (1-1-31) and (3-10) thiodicarb    51f)    (1-1-70) and (3-10) thiodicarb
25a)    (1-1-32) and (2-2) chlorpyrifos    52a)    (I-1-71) and (2-2) chlorpyrifos
25b)    (I-1-32) and (2-31) acephate    52b)    (I-1-71) and (2-31) acephate
25c)    (I-1-32) and (2-32) methamidophos    52c)    (1-1-71) and (2-32) methamidophos
25d)    (I-1-32) and (3-1) carbaryl    52d)    (1-1-71) and (3-1) carbaryl
25e)    (1-1-32) and (3-5) methiocarb    52e)    (1-1-71) and (3-5) methiocarb
25f)    (I-1-32) and (3-10) thiodicarb    520    (1-1-71) and (3-10) thiodicarb
26a)    (I-1-33) and (2-2) chlorpyrifos    53a)    (I-1-72) and (2-2) chlorpyrifos
26b)    (1-1-33) and (2-31) acephate    53b)    (1-1-72) and (2-31) acephate
26c)    (1-1-33) and (2-32) methamidophos    53c)    (I-1-72) and (2-32) methamidophos
 
- 25 -
No.    Active compound combination
comprising    No.
4-    Active compound combination
comprising
26d)    (1-1-33) and (3-1) carbaryl    53d)    (1-1-72) and (3-1) carbaryl
26e)    (1-1-33) and (3-5) methiocarb    53e)        (I-1-72) and (3-5) methiocarb
260    (1-1-33) and (3-10) thiodicarb    53f)        (I-1-72) and (3-10) thiodicarb
27a)        (I-1-38) and (2-2) chlorpyrifos   
27b)        (1-1-38) and (2-31) acephate   
27c)        (1-1-38) and (2-32) methamidophos   
27d)        (1-1-38) and (3-1) carbaryl   
27e)        (1-1-38) and (3-5) methiocarb   
270    (1-1-38) and (3-10) thiodicarb   

However, the general or preferred radical definitions or illustrations given above can also be
combined with one another as desired, i.e. including combinations between the respective ranges and
5 preferred ranges. They apply both to the end products and, correspondingly, to precursors and intermediates.
Preference according to the invention is given to active compound combinations comprising the compounds of the formula (1) and active compounds of the formulae (2-1) to (2-23) in which the 10 individual radicals are a combination of the meanings listed above as being preferred (preferable).
Particular preference according to the invention is given to active compound combinations
comprising the compounds of the formula (I) and active compounds of the formulae (2-1) to (2-23) in
which the individual radicals are a combination of the meanings listed above as being particularly
15    preferred.
Very particular preference according to the invention is given to active compound combinations
comprising the compounds of the formula (I) and active compounds of the formulae (2-1) to (2-23) in
which the individual radicals are a combination of the meanings listed above as being very
20 particularly preferred.
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, including in combination with heteroatoms, such as, for example, in alkoxy.
25
Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitutions the substituents can be identical or different.
 
-26-
In addition, the active compound combinations may also comprise further fungicidally, acaricidally or insecticidally active co-components.
5 If the active compounds in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. The mixing ratios required for fmding the synergism are not necessarily the preferred mixing ratios relevant for 100% activity. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, the combinations according to the invention
10 comprise active compounds of the formula (I) and the mixing partner of group 2 or of group 3 in the stated preferred and particularly preferred mixing ratios:
The mixing ratios are based on weight ratios. The ratio is to be understood as meaning active compound of the formula (I): mixing partner
Mixing partner    Preferred mixing ratio    Particularly preferred
mixing ratio
(2-1) azinphosmethyl    10:1 to 1:10    5:1 to 1:5
(2-2) chlorpyrifos    10:1 to 1:10    5:1 to 1:5
(2-3) diazinon    10:1 to 1:10    5:1 to 1:5
(2-4) dimethoate    10:1 to 1:10    5:1 to 1:5
(2-5) disulfoton    10:1 to 1:10    5:1 to 1:5
(2-6) ethion    10:1 to 1:10    5:1 to 1:5
(2-7) fenitrothion    10:1 to 1:10    5:1 to 1:5
(2-8) fenthion    20:1 to 1:10    5:1 to 1:5
(2-9) isoxathion    10:1 to 1:10    5:1 to 1:5
(2-10) malathion    10:1 to 1:10    5:1 to 1:5
(2-11) methidathion    10:1 to 1:10    5:1 to 1:5
(2-12) oxydemeton-methyl    10:1 to 1:10    5:1 to 1:5
(2-13) parathion    10:1 to 1:10    5:1 to 1:5
(2-14) parathion-methyl    10:1 to 1:10    5:1 to 1:5
(2-15) phenthoate    10:1 to 1:10    5:1 to 1:5
(2-16) phorate    10:1 to 1:10    5:1 to 1:5
(2-17) phosalone    10:1 to 1:10    5:1 to 1:5
(2-18) phosmet    10:1 to 1:10    5:1 to 1:5
(2-19) phoxim    10:1 to 1:10    5:1 to 1:5
(2-20) pirimiphos-methyl    10:1 to 1:10    5:1 to 1:5
(2-21) profenophos    10:1 to 1:10    5:1 to 1:5
 
- 27 -
Mixing partner    Preferred mixing ratio    Particularly preferred
mixing ratio
(2-22) prothiophos    10:1 to 1:10    5:1 to 1:5
(2-23) tebupyrimphos    10:1 to 1:10    5:1 to 1:5
(2-24) triazophos    5:1 to 1:20    1:1 to 1:10
(2-25) chlorfenvinphos    10:1 to 1:10    5:1 to 1:5
(2-26) dichlorphos    10:1 to 1:10    5:1 to 1:5
(2-27) dicrotophos    10:1 to 1:10    5:1 to 1:5
(2-28) mevinphos    10:1 to 1:10    5:1 to 1:5
(2-29) monocrotophos    10:1 to 1:10    5:1 to 1:5
(2-30) phosphamidon    10:1 to 1:10    5:1 to 1:5
(2-31) acephate    10:1 to 1:10    5:1 to 1:5
(2-32) methamidophos    10:1 to 1:10    5:1 to 1:5
(2-33) trichlorfon    10:1 to 1:10    5:1 to 1:5
(3-1) carbaryl    10:1 to 1:10    5:1 to 1:5
(3-2) fenoxycarb    10:1 to 1:10    5:1 to 1:5
(3-3) formetanate    10:1 to 1:10    5:1 to 1:5
(3-4) formetanate hydrochloride    10:1 to 1:10    5:1 to 1:5
(3-5) methiocarb    10:1 to 1:10    5:1 to 1:5
(3-6) methomyl    10:1 to 1:10    5:1 to 1:5
(3-7) oxamyl    5:1 to 1:100    1:1 to 1:20
(3-8) pirimicarb    10:1 to 1:10    5:1 to 1:5
(3-9) propoxur    10:1 to 1:10    5:1 to 1:5
(3-10) thiodicarb    5:1 to 1:20    1:1 to 1:10
The active compound combinations of the invention are suitable for controlling animal pests,
preferably arthropods and nematodes, in particular insects and arachnids, found in agriculture, in
animal health, in forests, in the protection of stored products and materials and in the hygiene sector.
5        They are active against normally sensitive and resistant species, and against all or individual
developmental stages. The abovementioned pests include:
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the Chilopoda, for example, Geophilus carpophagus, Scutigera spp. 10 From the order of the Symphyla, for example, Scutigerella immaculata.
From the order of the Thysanura, for example, Lepisma saccharina.
From the order of the Collembola, for example, Onychiurus armatus.
 
-28-
From the order of the Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
From the order of the Blattaria, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
5 From the order of the Dermaptera, for example, Forficula auricularia.
From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Phthiraptera, for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci, Thrips 10    palmi, Franldiniella accidentalis.
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes
vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,
15 Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius,
20 Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella,
25 Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana,
Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,
30 Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus
35    oryzophilus.
 
- 29 -
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila
melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp.,
 5 Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.
From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophyllus spp.
From the class of the Arachnida, for example, Scorpio maurus, Latrodectus mactans, Acarus siro,
10 Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
    15    The plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis,
Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp..
The active compound combinations can be converted into the customary formulations such as
 20 solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
These formulations are produced in a known manner, for example by mixing the active compounds
    25    with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that
is, emulsifiers and/or dispersants, and/or foam formers.
If the extender used is water, it is also possible, for example, to use organic solvents as cosolvents.
The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or
30 alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide,
    35    or else water.
 
- 30 -
Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolin, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and
5 dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, or else protein hydrolysates; suitable dispersants are: for example lignin-
10    sulfite waste liquors and methylcellulose.
Tacldfiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the
15    formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and
Prussian Blue, and organic colorants such as alizarin colorants, azo colorants and metal
phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
20 molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
25 The active compound combinations of the invention can be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances
30 produced by microorganisms, inter alia.
Mixtures with other known active compounds such as herbicides or with fertilizers and growth regulators are also possible.
35 When used as insecticides, the active compound combinations of the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these
 
- 31 -
formulations, as a mixture with synergists. Synergists are compounds which increase the action of the active compounds, without it being necessary for the synergist added to be active itself.
The active compound content of the use forms prepared from the commercially available
5 formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
The compounds are employed in a customary manner appropriate for the use forms.
10 When used against hygiene pests and stored-product pests, the active compound combinations are distinguished by an excellent residual action on wood and clay as well as good stability to alkali on limed substrates.
The active compound combinations of the invention are not only active against plant pests, hygiene
15 pests and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites) such as hard ticks, soft ticks, mange mites, harvest mites, flies (stinging and licking), parasitizing fly larvae, lice, head lice, bird lice and fleas. These parasites include:
From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
20 From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
From the order Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp.,
Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,
25 Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
30 From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattella 35    germanica, Supella spp.
 
- 32 -
From the subclass of the Acaria (Acarida) and the orders of the Meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.
5 From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
10
The active compound combinations of the invention are also suitable for controlling arthropods which attack agricultural livestock such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, honey-bees, other domestic animals such as, for example, dogs, cats, caged birds, aquarium fish and so-called experimental animals such as,
15 for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, cases of death and reductions in productivity (for meat, milk, wool, hides, eggs, honey and the like) should be diminished, so that more economical and simpler animal husbandry is possible by the use of the active compound combinations of the invention.
20 The active compound combinations of the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration such as, for example, by injections (intramuscularly, subcutaneously, intravenously, intraperitoneally and the like), implants, by nasal administration, by dermal administration in the form of, for example,
25 immersing or dipping, spraying, pouring-on, spotting-on, washing, dusting, and with the aid of active¬compound-comprising molded articles such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.
When used for cattle, poultry, domestic animals and the like, the active compound combinations can
30 be applied as formulations (for example powders, emulsions, flowables) comprising the active compounds in an amount of 1 to 80% by weight, either directly or after 100- to 10 000-fold dilution, or they may be used as a chemical dip.
Moreover, it has been found that the active compound combinations of the invention show a potent insecticidal action against insects which destroy industrial materials.
35
 
-33-
The following insects may be mentioned by way of example and with preference, but not by way of limitation:
Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium
rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus
5 brurmeus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.
Dermapterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur. Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes
10 flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
Bristle-tails such as Lepisma saccharina.
Industrial materials in the present context are understood as meaning non-living materials such as, 15 preferably, polymers, adhesives, glues, paper and board, leather, wood, timber products and paints.
The material which is to be protected from insect attack is very particularly preferably wood and timber products.
20 Wood and timber products which can be protected by the composition of the invention, or mixtures comprising it, are to be understood as meaning, for example:
Construction timber, wooden beams, railway sleepers, bridge components, jetties, vehicles made of
wood, boxes, pallets, containers, telephone poles, wood lagging, windows and doors made of wood,
plywood, chipboard, joinery, or timber products which quite generally are used in house construction
25    or building joinery.
The active compound combinations can be used as such, in the form of concentrates or generally
customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
30 The abovementioned formulations can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellant, if desired desiccants and UV stabilizers, and if desired colorants and pigments and other processing auxiliaries.
 
- 34 -
The insecticidal compositions or concentrates used for protecting wood and timber products comprise the active compound of the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
5 The amount of composition or concentrate employed depends on the species and the abundance of the insects and on the medium. The optimal quantity to be employed can be determined in each case by test series upon application. In general, however, it will suffice to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
10
A suitable solvent and/or diluent is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetter.
15 Organochemical solvents which are preferably employed are oily or oil-type solvents with an evaporation number of above 35 and a flash point of above 30°C, preferably above 45°C. Such oily and oil-type solvents which are insoluble in water and of low volatility and which are used are suitable mineral oils or their aromatic fractions or mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or alkylbenzene.
20
Mineral oils with a boiling range of 170 to 220°C, white spirit with a boiling range of 170 to 220°C, spindle oil with a boiling range of 250 to 350°C, petroleum and aromatics with a boiling range of 160 to 280°C, oil of turpentine, and the like are advantageously used.
25    In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180 to 210°C or
high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220°C and/or spindle oil and/or monochloronaphthalene, preferably a-monochloronaphthalene, are used.
The organic oily or oil-type solvents of low volatility and with an evaporation number of above 35
30 and a flash point of above 30°C, preferably above 45°C, can be replaced in part by organochemical solvents of high or medium volatility, with the proviso that the solvent mixture also has an evaporation number of above 35 and a flash point of above 30°C, preferably above 45°C, and that the mixture is soluble or emulsifiable in this solvent mixture.
35 In a preferred embodiment, some of the organochemical solvent or solvent mixture an aliphatic polar organochemical solvent or solvent mixture is replaced. Aliphatic organochemical solvents which
 
- 35 -
contain hydroxyl and/or ester and/or ether groups are preferably used, such as, for example, glycol ethers, esters or the like.
Organochemical binders used for the purposes of the present invention are the synthetic resins and/or
5 binding drying oils which are known per se and which can be diluted in water and/or dissolved or dispersed or emulsified in the organochemical solvents employed, in particular binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol resin, hydrocarbon resin such as indene/coumarone resin, silicone resin, drying vegetable
10    and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.
The synthetic resin employed as binder can be employed in the form of an emulsion, dispersion or
solution. Bitumen or bituminous substances may also be used as binders, in amounts of up to 10% by
weight. In addition, colorants, pigments, water repellants, odor-masking agents, and inhibitors or
15    anticorrosive agents and the like, all of which are known per se, can be employed.
In accordance with the invention, the composition or the concentrate preferably comprises, as
organochemical binders, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil.
Alkyd resins which are preferably used in accordance with the invention are those with an oil content
20 of over 45% by weight, preferably 50 to 68% by weight.
Some or all of the abovementioned binder can be replaced by a fixative (mixture) or plasticizer
(mixture). These additives are intended to prevent volatilization of the active compounds, and also
crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of
25 binder employed).
The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl
phthalate or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic esters such as
di(2-ethylhexyl)adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate,
30    glycerol ethers or higher-molecular-weight glycol ethers, glycerol esters and p-toluenesulfonic esters.
Fixatives are based chemically on polyvinyl alkyl ethers such as, for example, polyvinyl methyl ether, or ketones such as benzophenone and ethylenebenzophenone.
35    Other suitable solvents or diluents are, in particular, water, if appropriate as a mixture with one or
more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
 
- 36 -
Particularly effective timber protection is achieved by industrial-scale impregnating processes, for example the vacuum, double-vacuum or pressure processes.
5 The active compound combinations of the invention can at the same time be employed for protecting objects which come into contact with saltwater or brackish water, such as hulls, screens, nets, buildings, moorings and signaling systems, against fouling.
Fouling by sessile Oligochaeta, such as Serpulidae, and by shells and species from the Ledamorpha
10 group (goose barnacles), such as various Lepas and Scalpellum species, or by species from the Balanomorpha group (acorn barnacles), such as Balanus or Pollicipes species, increases the frictional drag of ships and, as a consequence, leads to a marked increase in operation costs owing to higher energy consumption and additionally frequent stops in the dry dock.
15 Apart from fouling by algae, for example Ectocarpus sp. and Ceramium sp., fouling by sessile Entomostraka groups, which come under the generic term Cirripedia (cirriped crustaceans), is of particular importance.
Surprisingly, it has now been found that the active compound combinations of the invention have an 20    outstanding antifouling action.
Using the active compound combinations of the invention allows the use of heavy metals such as, for
example, in bis(trialkyltin) sulfides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper(I) oxide,
triethyltin chloride, tri-n-buty1(2-pheny1-4-chlorophenoxy)fin, tributyltin oxide, molybdenum
25 disulfide, antimony oxide, polymeric butyl titanate, phenyl(bispyridine)bismuth chloride, tri-n-butyltin fluoride, manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol 1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate, zinc oxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides to be dispensed
30 with, or the concentration of these compounds to be substantially reduced.
If appropriate, the ready-to-use antifouling paints can additionally comprise other active compounds, preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.
35 Preferable suitable components in combinations with the antifouling compositions according to the invention are:
 
- 37 -
algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophen, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
fungicides such as benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide, dichlofluanid,
    5    fluorfolpet, 3-iodo-2-propinyl butylcarbamate, tolylfluanid and azoles such as azaconazole,
cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole; molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and trimethacarb;
or conventional antifouling active compounds such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one,
10 diiodomethylparatryl sulfone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide, pyridine/triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.
15 The antifouling compositions used comprise the active compound combinations of the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
Moreover, the antifouling compositions of the invention con    p ise the customary components such as,
for example, those described in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling 20 Marine Coatings, Noyes, Park Ridge, 1973.
Besides the algicidal, fungicidal, molluscicidal active compounds and insecticidal active compounds of the invention, antifouling paints comprise, in particular, binders.
    25    Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a
solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride/vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene/styrene/acrylonitrile rubbers, drying oils such as linseed oil, resin esters or modified hardened resins in combination with tar or bitumens, asphalt and epoxy compounds, small
30 amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.
If appropriate, paints also comprise inorganic pigments, organic pigments or colorants which are
preferably insoluble in salt water. Paints may furthermore comprise materials such as colophonium to
allow controlled release of the active compounds. Furthermore, the paints may comprise plasticizers,
35 modifiers which affect the rheological properties and other conventional constituents. The
compounds of the invention or the abovementioned mixtures may also be incorporated into self-
 
-38-
polishing antifouling systems.
The active compound combinations are also suitable for controlling animal pests, in particular
insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings,
5 factory halls, offices, vehicle cabins and the like. They can be employed in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include:
From the order of the Scorpionidea, for example, Buthus occitanus.
From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp.,
10 Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
From the order of the Araneae, for example, Aviculariidae, Araneidae.
From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones 15    cheiridium, Opiliones phalangium.
From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber.
From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp.
From the order of the Chilopoda, for example, Geophilus spp.
From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes 20    inquilinus.
From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
From the order of the Saltatoria, for example, Acheta domesticus.
25 From the order of the Dermaptera, for example, Forficula auricularia.
From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp.
From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp.
From the order of the Coleptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus 30 oryzae, Sitophilus zeamais, Stegobium paniceum.
From the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
35 From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
 
- 39 -
From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
5 From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
10 They are used as aerosols, pressureless spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.
15
According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic
20 engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include
25 harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
The treatment of the invention of the plants and parts of plants with the active compounds is carried
out directly or by action on their environment, habitat or storage area according to customary
30 treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.
As already mentioned above, it is possible to treat all plants and their parts according to the invention.
35 In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional
biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated. In a
 
- 40 -
further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms "parts", "parts of plants" and "plant parts" have been explained above.
5    Particularly preferably, plants of the plant cultivars which are in each case commercially available or
in use are treated according to the invention.
Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate,
vegetation period, diet), the treatment of the invention may also result in superadditive ("synergistic")
10 effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional
15        value of the harvested products, better storage stability and/or processability of the harvested products
are possible which exceed the effects which were actually to be expected.
The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are
preferred and to be treated according to the invention include all plants which, in the genetic
20 modification, received genetic material which imparts particularly advantageous useful traits to these
plants. Examples of such traits are better plant growth, increased tolerance to high or low
temperatures, increased tolerance to drought or to water or soil salt content, increased flowering
performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a
higher nutritional value of the harvested products, better storage stability and/or processability of the
25 harvested products. Further and particularly emphasized examples of such traits are a better defense
of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic
fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active
compounds. Examples of transgenic plants which may be mentioned are the important crop plants,
such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, tobacco, oilseed rape and also fruit
30 plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to
maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are particularly emphasized
are the increased defense of the plants against insects, arachnids, nematodes and worms by toxins
formed in the plants, in particular those formed in the plants by the genetic material from Bacillus
thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIlA, CrylDB2,
35 Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as "Bt
plants"). Traits that are also particularly emphasized are the increased defense of plants against fungi,
 
- 41 -
bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example
5 the "PAT" gene). The genes in question which impart the desired traits can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgarde (cotton), Nucotn® (cotton) and
10 NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, for example maize). Herbicide-resistant plants (plants bred in a
15 conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these or still-to-be-developed genetic traits, which plants will be developed and/or marketed in the future.
20 The plants listed can be treated according to the invention in a particularly advantageous manner with the active compound mixtures of the invention. The preferred ranges stated above for the mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the mixtures specifically mentioned in the present text.
25 The good insecticidal and acaricidal action of the active compound combinations of the invention can be seen from the examples which follow. While the individual active compounds show weaknesses in their action, the combinations show an action which exceeds a simple sum of actions.
A synergistic effect in insecticides and acaricides is always present when the action of the active 30 compound combinations exceeds the total of the actions of the active compounds when applied individually.
The expected action for a given combination of two active compounds can be calculated according to S.R. Colby, Weeds 15 (1967), 20-22):
35
 
- 42 -
If
X    is the kill rate, expressed as a percentage of the untreated control, when employing active
compound A at an application rate of m g/ha or in a concentration of m ppm,
Y    is the kill rate, expressed as a percentage of the untreated control, when employing active
5    compound B at an application rate of n g/ha or in a concentration of n ppm and
E    is the kill rate, expressed as a percentage of the untreated control, when employing active
compounds A and B at application rates of m and n g/ha or in a concentration of m and n ppm,
then
    E=X Y -    X .y
10        100

If the actual insecticidal kill rate exceeds the calculated value, the action of the combination is superadditive, i.e. a synergistic effect is present. In this case, the actually observed kill rate must exceed the value calculated using the above formula for the expected kill rate (E).
15
After the desired period of time, the kill in % is determined. 100% means that all animals have been killed; 0% means that none of the animals have been killed.
 
- 43 -
Use examples Example A
5 Myzus persicae test
Solvent:    7 parts by weight of dimethylformamide
Emulsifier:    2 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed 10 with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) which are heavily infested by the green peach aphid (Myzus persicae) are treated by being dipped into the preparation of active compound of the desired concentration.
15 After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. The determined kill ratios are entered into Colby's formula (see page 42).
In this test, for example, the following active compound combination according to the present application shows a synergistically enhanced activity compared to the active compounds applied on 20 their own:
Table A
Plant-damaging insects
Myzus persicae test
Active compounds        Concentration of active
compound in ppm    Kill rate in
1
found*    % after
d
talc.**
H3C
-■
H3C    N    .../
CI .    CI
H3C 0    /
CF3    (I-1-9)    4    0    
S
    FI5C20.1 IA    CI
7    I
    H5C20 a    "/-    ci
(2-2) chlorpyrifos        0.8    65   
(1-1-9) + (2-2) chlorpyrifos (5:1)        4 + 0.8    85    65

* found.    = activity found
** talc.    = activity calculated using Colby's formula
 
WO 2005/053406    PCT/EP2004/013197
- 44 -
Claims
1.    A composition comprising a synergistically effective active compound combination of
anthranilamides of the formula (1)
3    2
5     

in which
Al and A2 independently of one another represent oxygen or sulfur,
X1    represents N or CR10,
R'    represents hydrogen or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or
10    C3-C6-cycloalkyl, each of which is optionally mono- or polysubstituted, where the
substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylthio, CI-Cr alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C4-alkoxycarbonyl, C1-C4-alkylamino, C2-C8- dialkylamino, C3-C6-cycloalkylamino, (C1-C4-alkyl)-C3-C6-cycloalkylamino and R11,
15 R2 represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1¬C4-alkoxy, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C2-C6- alkoxycarbonyl or C2-C6-alkylcarbonyl,
R3    represents hydrogen, R11 or represents Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-
C6-cycloallcyl, each of which is optionally mono- or polysubstituted, where the
20        substituents independently of one another may be selected from the group consisting
of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy,
C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C6-alkoxycarbonyl, C2-C6- alkylcarbonyl, C3-C6-trialkylsilyl, R", phenyl, phenoxy and a 5- or 6-membered heteroaromatic ring, where each phenyl, phenoxy and 5- or 6-membererd
25 heteroaromatic ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12, or
R2 and R3 may be attached to one another and form the ring M,
 
- 45 -
represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci¬C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio,
C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfmyl, Ci-
 5 C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-diallcylamino, C3-C6-cycloalkylamino, C3-C6-trialkylsily1 or represents phenyl, benzyl or phenoxy, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2' Cralicynyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl,
 10 C3-C6-halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloallcoxy, C1-C4- alkylthio, C1-C4-alkylsulfinyl, CI-Cralkylsulfonyl, C1-C4-alkylamino, C2-C8- dialkylamino, C3-C6-cycloalkylamino, C3-C6-(alkyl)cycloalkylamino, C2-C4- alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl, C3-C8- dialkylaminocarbonyl and C3-C6-trialkylsilyl,
    15    R5 and R8 in each case independently of one another represent hydrogen, halogen or represent
in each case optionally substituted C1-C4-alkyl, C1-C4-haloalkyl, R12, G, J, -OJ, -OG, -S(0)P-J, -S(0)PG, -S(0)p-phenyl, where the substituents independently of one another may be selected from one to three radicals W or from the group consisting of R12, Ci-C10-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy and C1-C4-alkythio,
 20 where each substituent may be substituted by one or more substituents independently of one another selected from the group consisting of G, J, R6, halogen, cyano, nitro, amino, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio,
C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1¬C4-haloalkylsu1fonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-trialkylsilyl,
 25 phenyl and phenoxy, where each phenyl or phenoxy ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
G    in each case independently of one another represent a 5- or 6-membered non-
aromatic carbocyclic or heterocyclic ring which may optionally contain one or two
 30 ring members from the group consisting of C(=O), SO and S(=0)2 and which may optionally be substituted by one to four substituents independently of one another selected from the group consisting of C1-C2-alkyl, halogen, cyano, nitro and C1-C2- alkoxy, or independently of one another represent C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, (cyano)-C3-C7-cycloalkyl, (C1-C4-alky1)-C3-C6-cycloalkyl, (C3-C6-
    35    cycloalkyl)-C1-C4-alkyl, where each cycloalkyl, (alkyl)cycloalkyl and (cycloalkyl)-
alkyl may optionally be substituted by one or more halogen atoms,
 
- 46 -
J    in each case independently of one another represent an optionally substituted 5- or 6-
membered heteroaromatic ring, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
R6    independently of one another represent -C(=E1)R19, -LC(=E1)R19, -C(=E1)LR19,
 5 -LC(=E1)LR19, -0P(=Q)(0R19)2, -SO2LR" or -LSO2LR19, where each E' independently of one another represents 0, S, N-R15, N-OR15, N-N(R15)2, N-S=0, N¬CN or N-NO2,
R7    represents hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, halogen, C1-C4-alkoxy, Ci-C4-
haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfmyl, C1-C4-alkylsulfonyl,
    1 0    alkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl,
R9    represents C1-C4-haloalkyl, Cl-C4-haloalkoxy, C1-C4-haloalkylsulfinyl or halogen,
le°    represents hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, halogen, cyano or Ci-C4-
haloalkoxy,
R11    in each case independently of one another represents in each case optionally mono-
 15 to trisubstituted C1-C6-alkylthio, C1-C6-alkylsulfenyl, C1-C6-haloalkythio, C1-C6- haloalkylsulfenyl, phenylthio or phenylsulfenyl, where the substituents independently of one another may be selected from the list W, -S(0)„N(R16)2, -C(=0)R13, -L(C=0)R1 4, -S(C)LR14, -C(=O)LR'3, -S(0)NR13C(=0)R", -S(0),NR13q=0)LR14 or -S(0)„NR13S(0)2LR14,
    20    L    in each case independently of one another represents 0, NR" or S,
R12    in each case independently of one another represents -B(OR17)2, amino, SH,
thiocyanato, C3-C8-trialkylsilyloxy, CI-C4-alkyl disulfide, -SF5, -C(=E)R19, -LC(=E)R19, -C(=E)LR19, -LC(=E)LR'9, -0P(=Q)(012.19)2, -SO2LR19 or -LSO2LR19,
Q    represents 0 or S,
    25    R"    in each case independently of one another represent hydrogen or represent in each
case optionally mono- or polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4- alkoxy, C1-C4-allcylsulfmyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-
    30    dialkylamino, C3-C6-cycloalkylamino or (C1-C4-alkyl)-C3-C6-cycloalkylamino,
R14    in each case independently of one another represent in each case optionally mono- or
polysubstituted    C2-C20-alkenyl, C2-C20-alkynyl or C3-C6-cycloalkyl,
where the substituents independently of one another may be selected from the group
consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylsulfinyl,
    35    C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino
and (C1-C4-alkyl)-C3-C6-cycloalkylamino or represent optionally substituted phenyl,
 
- 47 -
where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
R15    in each case independently of one another represent hydrogen or represent in each
case optionally mono- or polysubstituted C1-C6-haloalkyl or C1-C6-alkyl, where the
 5 substituents independently of one another may be selected from the group consisting of cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-allcylthio, C1-C4- alkylsulfmyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C2-C6- alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl and optionally substituted
 10 phenyl, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12, or N(R15)2 represents a cycle which forms the ring M,
R16    represents CI-C12-alkyl or C1-C12-haloalkyl, or N(R16)2 represents a cycle which
forms the ring M,
    15    R17    in each case independently of one another represent hydrogen or C1-C4-alkyl, or
B(OR17)2 represents a ring in which the two oxygen atoms are attached via a chain having two to three carbon atoms which are optionally substituted by one or two substituents independently of one another selected from the group consisting of methyl and C2-C6-alkoxycarbonyl,
    20    R18    in each case independently of one another represent hydrogen, C1-C6-alkyl or C1-C6-
haloalkyl, or N(R13)(R18) represents a cycle which forms the ring M,
R19    in each case independently of one another represent hydrogen or represent in each
case mono- or polysubstituted C1-C6-alkyl, where the substituents independently of
one another may be selected from the group consisting of cyano, nitro, hydroxyl,
 25 C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4- alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfmyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, CO211, C2-C6-alkoxycarbonyl, C2-C6- alkylcarbonyl, C3-C6-triallcylsily1 and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals
    30    W, C1-C6-haloalkyl, C3-C6-cycloalkyl or phenyl or pyridyl, each of which is
optionally mono- to trisubstituted by W,
M    in each case represents an optionally mono- to tetrasubstituted ring which, in addition
to the nitrogen atom attached to the substituent pair R13 and R18, (R15)2 or (R16)2, contains two to six carbon atoms and optionally additionally a further nitrogen,
    35    sulfur or oxygen atom, where the substituents independently of one another may be
 
-48-
selected from the group consisting of Ci-C2-alkyl, halogen, cyano, nitro and C1-C2- alkoxy,
W    in each case independently of one another represent C1-C4-alkyl, C2-C4-alkenyl,
C2-C4-alkynyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-
    5    haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, Cl-C4-alkoxy, C1-C4-
haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfonyl, C1-C4- allcylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, (Ci-C4-alkyl)-C3-C6- cycloallcylamino, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, CO2H, C2-C6-alkylaminocarbonyl, C3-C8-dialkylaminocarbonyl or C3-C6-trialkylsilyl,
    10    n    in each case independently of one another represent 0 or 1,
p    in each case independently of one another represent 0, 1 or 2,
where, if (a) R5 represents hydrogen, C1-C6-alkyl, Cl-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-
haloalkynyl, C1-C4-haloalkoxy, Ci-C4-haloalkylthio or halogen and (b) R8 represents
 15 hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkYnYl, Ci-C4- haloalkoxy, C1-C4-haloalkylthio, halogen, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6¬alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl, (c) at least one substituent selected from the group consisting of R6, R11 and 11'2 is present and (d) if R'2 is not present, at least one of the radicals R6 and R1' is different from C2-C6-alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6-
    20    alkylaminocarbonyl and C3-C8-dialkylaminocarbonyl, and
where the compound of the general formula (1) may also be an N-oxide or salt,
and at least one insecticidally active compound of groups 2 and 3 below selected from A)    (thio)phosphates (group 2), preferably
    25    (2-1) azinphos-methyl (known from US 2,758,115)
N
FI,CO„SN
I
 FI,C0 S
and/or
(2-2) chlorpyrifos (known from US 3,244,586)
S
FI5C20-1 1,0    CI
HA° ci    CI
    30    and/or
(2-3) diazinon (known from US 2,754,243)
 
- 49 -
H3C
0—P-0C H
)=-N    2 5
OC,H,
(H3C)2CH
and/or
(2-4) dimethoate (known from US 2,494,283)
0
II    II
H3C-N-C-CHFs-1)—OCH3
H    OCH3
and/or
(2-5) disulfoton (known from DE-A 91 76 68)
HSO20,
SiFs/\ CH,
0C2H5
and/or
(2-6) ethion (known from US 2,873,228)
0C2H5    0C2H5
and/or
(2-7) fenitrothion (known from BE-A 0 594 669)
S „OCH3 P
02N    °0 H3
H3C
ad/or
(2-8) fenthion (known from DE-A 11 16656)
//    SCH3
H3C0-1■0 H3C0 and/or
(2-9) isoxathion (known from DE-A 15 67 137) N-0
H5C20-,p,0
oc2H,
20    and/or
(2-10) malathion (known from US 2,578,562)
 
- 50 -
0
I I s
OCH,'    0
0 OC,H,
and/or
(2-11) methidathion (known from DE-A 16 45 982)
OCH3
    I I s    S
    OCH3    0
and/or
(2-12) oxydemeton-methyl (known from DE-A 94 73 68)
0
,C2H5
H3CO—T.s.s/NA-0
H3C0
and/or
(2-13) parathion (known from DE-A 81 41 52)
H,C20
\ S
P'
    H5C20 0    NO2
and/or
(2-14) parathion-methyl (lmown from DE-A 81 41 42) H3CON _s
    H3C0/ \O    NO2
 
and/or
(2-15) phenthoate (known from GB-A 834 814)
H
3
CHO
OC,H,
and/or
(2-16) phorate (known from US 2,586,655)
C2 H5
H,C,S,
—0C2H,
20    and/or
(2-17) phosalone (known from DE-A 24 31 192)
 
S
I
H5C20— P
H5C20    N
0
0         CI    - 51 -

and/or
(2-18) phosmet (known from US 2,767,194)
0    S
N—CH2S—rOCH3
OCH3
5    and/or
(2-19) phoxim (known from DE-A 12 38 902)
IsI    ,N
H,C20—P-0"
CN
OC2H,
and/or
(2-20) pirimiphos-methyl (known from DE-A 14 45 949) H3C4 0    CH3
1
H3CO
10    H5Cr    C2H5
,N,
and/or
(2-21) profenophos (known from DE-A 22 49 462)
0
H3C    0
H5C20) a    Br
and/or
15    (2-22) prothiophos (known from DE-A 21 11 414)
H3C
H5C20
CI    CI
 
-52-
and/or
(2-24) triazophos (known from DE-A 12 99 924)
H3C204oN,,N
H5C20     

and/or
5    (2-25) chlorfenvinphos (known from US 2,956,073)
0
I I
H3C20
CI
and/or
(2-26) dichlorphos (known from GB-A 775 085)
0    CI
OCH3
10    and/or
(2-27) dicrotophos (known from BE-A 55 22 84)
H3C0\8
P-0
11,C0
H3C
and/or
(2-28) mevinphos (known from US 2,685,552)
H3C0\8
P-0    CO2CH3
H3C0
15    H3C    H
and/or
(2-29) monocrotophos (known from DE-A 19 64 535) H3C0 I/O‘(CH3
P-0    I
H3C0
H3C
and/or
20    (2-30) phosphamidon (known from US 2,908,605)
 
- 53 -
H3C08O    p21-15
    ,P-0    N ■
H3C0    C2H5
    H3C    CI
and/or
(2-31) acephate (known from DE-A 20 14 027)
0 H3C—S,W,N,f0
OCH3 CH,
5    and/or
(2-32) methamidophos (known from US 3,309,266)
O
01 CH3
and/or
(2-33) trichlorfon (known from US 2,701,225)
0 Td13
,C.
,P OH
H3C0 \OCH,
and/or
B)    carbamates (group 3), preferably
(3-1) carbaryl (known from US 2,903,478)
15     

and/or
20    (3-3) formetanate (known from DE-A 11 69 194)
pH3 N=C—N
0    H \CH,
H3C—N—C-0
 
- 54 -
and/or
(3-4) formetanate hydrochloride (known from DE-A 11 69 194) and/or
(3-5) methiocarb (known from DE-A 11 62 352)
H
,N    CH3
H3C
SCH3
5    CH3
and/or
(3-6) methomyl (known from US 3,639,620) 0
H3C,.    S,. CH 3
CH3
and/or
10    (3-7) oxamyl (known from DE-A 17 68 623)
 
and/or
(3-8) pirimicarb (= Pirimor) (known from GB-A 1 181 657) CH3    ?H3
H3    0yN,CH,
0
,
H3CN, CH3
15    and/or
(3-9) propoxur (known from DE-A 11 08 202)
CH3
,,N
H3C y
O
and/or
(3-10) thiodicarb (known from DE-A 25 30 439) CH    0    0    CH
S    .,    S
I 3    I    3
y' , 0)1, N,s N O„ *1-
I    I
CH3    CH3 CH3    CH3
20
 
-55-
2.    The composition as claimed in claim 1 comprising at least one active compound from the
group of the anthranilamides of the formula (I-1) in which
1R2 R3 —N
in which
    5    R2    represents hydrogen or C1-C6-alkyl,
R3    represents C1-C6-alkyl which is optionally substituted by one R6,
R4    represents C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or halogen,
R5    represents hydrogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or halogen,
R6    represents -C(=E2)R19, -LC(=E2)R19, - C(=E2)LR19 or -LC(=E2)LR19, where each E2
    10    independently of one another represents 0, S, N-12.15, N-OR15, N-N(R15)2, and each L
independently of one another represents 0 or NR1 8,
R7    represents C1-C4-haloalkyl or halogen,
R9    represents C1-C2-haloalkyl, C1-C2-haloalkoxy, S(0),-C1-C2-haloalkyl or halogen,
R15    in each case independently of one another represent hydrogen or represent in each
 15 case optionally substituted Cl-C6-haloalkyl or C1-C6-alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4- alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfmyl and C1-C4- haloalkylsulfonyl,
    20    R18    in each case represents hydrogen or C1-C4-alkyl,
R19    in each case independently of one another represent hydrogen or C1-C6-alkyl,
p    independently of one another represent 0, 1, 2.
3.    The composition as claimed in claim 1 or 2 comprising at least one active compound from
    25    group 2 and/or group 3 selected from
(2-2) chlorpyrifos,
(2-31) acephate,
(2-32) methamidophos,
(3-1) carbaryl,
    30    (3-5) methiocarb,
(3-10) thiodicarb.
 
-56-
4.    The composition as claimed in claim 1, 2 or 3 comprising anthranilamides of the formula (1)
and at least one active compound from group 2 and/or group 3 in a ratio of 50:1 to 1:50.
5    5.    The use of a synergistically effective mixture as defined in claim 1, 2, 3 or 4 for controlling
animal pests.
6.    A process for preparing pesticides, characterized in that a synergistically effective mixture as
defined in claim 1, 2, 3 or 4 is mixed with extenders and/or surfactants.
10
7.    A method for controlling animal pests, characterized in that synergistically effective mixtures
as defined in claim 1, 2, 3 or 4 are allowed to act on animal pests and/or their habitat.

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