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(11) Patent Number: la 302 (45) Date of grant: 23/02/2009
Kenya Industrial Property Institute.
(73) Owner(s): Bayer Cropscience Aktiengesellschaft of Alfred-Nobel-Str. 50,40789 Monheim, Germany
(72) Inventor(s)
(74)Agent/address for correspondence:    FISCHER, RUDIGER; FUNKE,CHRISTIAN; FISCHER,REINER; HUNGENBERG ,HEIKE; ANDERSCH, WOLFRAM; THIELERT, WOLFGANG and KRAUS, ANTON
Kaplan & Stratton Advocates,
(54) Title:    COMBINATION OF ACTIVE SUBSTANCES WITH INSECTICIDAL
PROPERTIES
(57) Abstract: The invention relates to novel insecticidal combinations of active substances comprising anthrananilic acid amides and other insecticidal active substances from the group of pyrethroids. Said combinations are highly suitable for combatting pests such as insects.
 
-1-
 
Combination of active substances with insecticidal properties
The invention relates to novel insecticidal active compound combinations consisting, firstly, of known anthranilamides and, secondly, of further known insecticidally active compounds, which combinations are highly suitable for controlling animal pests, such as insects.
It is already known that certain anthranilamides have insecticidal properties (WO 01/70671, 5 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).
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 that numerous heterocycles, organotin compounds, benzoylureas 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 (I) R3N,R2
 

 
in which
A' and A2 independently of one another represent oxygen or sulfur,
20    X1    represents N or CR'°,
represents hydrogen or represents in each case optionally mono- or polysubstituted CI-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, C,-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkyl-
25    sulfonyl, C2-C4-alkoxycarbonyl, C,-C4-alkylamino, C2-Cg-dialkylamino, C3-C6-cycloalkyl-
amino, (CI-C4-allcyl)C3-C6-cycloallcylamino and R",
 
-2-
R2    represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C4-
alkoxy, C1-C4-allcylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C2-C6-alkoxy-carbonyl or C2-C6-alkylcarbonyl,
R3    represents hydrogen, R" or represents in each case optionally mono- or polysubstituted
    5    C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, 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-haloalkoxy, C1-C4-alkylthio,
sulfmyl, C1-C4-alkylsulfonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkyl¬silyl, R11, phenyl, phenoxy and a 5- or 6-membered heteroaromatic ring, where each
 10 phenyl, phenoxy and 5- or 6-membered 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 m_ay 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, C1-C4-allcylsulfinyl, C1-C4-allcylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-allcylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C3-C6-trialkylsilyl or represents in each case optionally mono- or polysubstituted phenyl, benzyl or phenoxy,
 20 where the 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, C1-C4-haloallcyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, Ci-Ca¬alkoxy, C1-C4-haloalkoxy, C1-C4-allcylthio, C1-C4-alkylsulfiny I, C1-Ca-alkylsulfonyl, C1-C4¬alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C3-C6-(allcyl)cycloalkylamino,
    25    C2-C4-allcylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl, C3-C8-dialkyl-
aminocarbonyl and C3-C6-triallcylsilyl,
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, R'2, G, J, -OJ, -00,
-S(0)Pphenyl, where the substituents independently of one another may be
 .30 selected from one to three radicals W or from the group consisting of le, 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 0, J, R6, halogen, cyano, nitro, amino, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, CI-Cralkylsulfonyl, C1-C4-halo-
    35    alkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloallcylsulfonyl,    C2-C8-
diallcylamino, C3-C6-trialkylsilyl, phenyl and phenoxy, where each phenyl or phenoxy ring
 
-3-
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 nonaromatic
carbocyclic or heterocyclic ring which optionally contains one or two ring members from
 5 the group consisting of C(=0), 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 C,-C2-alkyl, halogen, cyano, nitro and C,-C2-alkoxy, or independently of one another represent C2-C6-alkenyl, C2-C6-allcynyl, C3-C7-cycloalkyl, (cyano)C3-C7-cycloalkyl, (CI-C4- allcyl)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,
J    in each case independently of one another represent an optionally substituted 5- or 6-
em
mbered heteroaromatic ring, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals 12.'2,
    15    R6    independently of one another represent -C(=E1)R19, -LC(=E1)R19, _C(=E1)LR19,
-LC(=E1)LR19, -0P(=Q)(0R19)2, -SO2L1218 or -LSO2LR19, where each E' independently of the others represents 0, S, N-R15, N-012.15, N-N(R15)2, N-S=O, N-CN or N-NO2,
represents hydrogen, C,-C4-alkyl, C1-C4-haloalkyl, halogen, C,-C4-alkoxy,
alkoxy,    C,-C4-alkylsulfinyl,    C,-C4-haloalkylthio,
    20    C,-C4-haloalkylsulfonyl,
R9    represents C,-C4-haloalkyl, C,-C4-haloalkoxy, C,-C4-haloalkylsulfinyl or halogen,
R'°
R1'
in each case independently of one another represent in each case optionally mono- to,
trisubstituted C,-C6-alkylthio, C1-C6-alkylsulfenyl, C,-C6-haloalkythio, C,-C6-halo-
25 alkylsulfenyl, phenylthio or phenylsulfenyl, where the substituents independently of one another may be selected from the list consisting of W, -S(0)nN(R16)2, -C(=0)R13, -L(C=0)R14, -S(C=0)1,R14, -C(=0)LR13, -S(0)nN12.13C(=0)R13, -S(0)nNR13C(=0)LR" and -S(0)nNeS(0)2Lle,
L    in each case independently of one another represent 0, NR18 or S,
30    R12    in each case independently of one another represent -B(OR17)2, amino, SH, thiocyanato,
C3-C8-trialkylsilyloxy, C,-C4-alkyl disulfide, -SF5, -C(=E)R19, -LC(=E)R19, -C(=E)LR19, -LC(=E)LR19, -0P(=Q)(012.19)2, -SO2LR19 or -LSO2LR19,
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    C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-
cycloallcyl, 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 and (C1-C4-allcyl)C3-C6-cycloalkylamino,
Ria    in each case independently of one another represent in each case mono- or polysubstituted
 5 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-alky lsulfinyl, C1-C4-alkylsulfonyl, C1-C4- alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino and (Ci-C4-alkyl)C3-C6-cyclo-alkylarnino 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
maw- or polysubstituted C1-C6-haloalkyl or CI-C6-alkyl, where the substituents
independently of one another may be selected from the group consisting of cyano, nitro,
 15 hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, 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- 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 R12, or
    20    N(R15)2 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,
R'7    in each case independently of one another represent hydrogen or Ci-C4-alkyl, or B(OR17)2
represents a ring, where the two oxygen atoms are attached via a chain to two or 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, CI-C6-alkyl or C1-C6-
haloalkyl, or N(R")(e) represents a cycle which forms the ring M,
R19    in each case independently of one another represent hydrogen or represent in each case
 30 optionally mono- or polysubstituted CI-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-alkylsulfinyl, CI -C4-alkylsulfonyl, C1-C4- haloallcylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, CI-C4-alkylamino, C2-C8- diallcylamino, CO2H, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl and
    35    optionally substituted phenyl, where the substituents independently of one another may be
selected from one to three radicals W, C1-C6-haloalkyl, C3-C6-cycloalkyl or phenyl or
 
-5-
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 which is 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, sulfur or oxygen atom, and where the substituents independently of one another may be selected from the group consisting of CI-C2-alkyl, halogen, cyano, nitro and C1-C2-alkoxy,
in each case independently of one another represent CI-CI-alkyl, C2-C4-alkenyl, C2-C4- allcynyl, C3-C6-cycloalkyl,    C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-
halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio,
10 C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4alkylamino, C2-C8-dialkylamino, C3-C6- cycloallcylamino, (C1-C4-alkyl)C3-C6-cycloalkylamino, C2-C4-allcylcarbonyl, C2-C6-alkoxy¬carbonyl, CO2H, C2-C6-alkylaminocarbonyl, C3-Cg-dialkylaminocarbonyl or C3-C6- trilkylsilyl,
n    in each case independently of one another represent 0 or 1,
15    p    in each case independently of one another represent 0, 1 or 2,
where in the case that (a) R5 represents hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl,
C2-C6-haloalkynyl, C1-C4-haloalkoxy, C1-C4-haloalicylthio or halogen and (b) R8 represents hydrogen,
CI-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C4-haloalkoxy, C1-C4-halo-
20 alkylthio, halogen, C2-C4-allcylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl, (c) at least one substituent selected from the group consisting of R6, R" and R12 is present and (d), if R12 is not present, at least one R6 or R" is different from C2-C6- alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6-alkylaminocarbonyl and C3-C8-diallcylaminocarbonyl, and
25    the compounds of the general formula (I) also include N-oxides and salts,
and at least one active compound from the group of the pyrethroids (active compounds of group 2) is synergistically effective and suitable for controlling animal pests.
30    Depending inter alia on the nature of the substituents, the compounds of the formula (1) may be
present as geometrical and/or optical isomers or isomer mixtures of varying composition which, if appropriate, may be separated in a customary manner. The present invention proN4des both the pure isomers and the isomer mixtures, their preparation and use and also compositions comprising them. However, hereinbelow, for the sake of simplicity, only compounds of the formula (I) are referred to,
35        although what is meant are both the pure compounds and, if appropriate, also mixtures having
varying proportions of isomeric compounds.
 
- 6 -
Preference is given to active compound combinations comprising compounds of the formula (I-1)
 
    5    in which
R2    represents hydrogen or C,-C6-alkyl,
R3    represents C,-C6-alkyl which is optionally substituted by a radical R6,
R4    represents C,-C4-alkyl, C,-C2-haloalkyl, C,-C2-haloalkoxy or halogen,
R5    repfesents hydrogen, Cs-Cs-alkyl, C,-C2-haloalkyl, CI-C2-harollkoxy or halogen,
    10    R6    represents -C(=E2)11.19, -LC(=E2)R19, _c(=E2)L.,K 19
 or -LC(=E2)LR19, where each E2 independently of the others represents 0, S, N-R15, N-OR15, N-N(R15)2, and each L independently of the others represents 0 or NR18,
R7    represents C,-C4-haloalkyl or halogen,
R9    represents C,-C2-haloalkyl, C,-C2-haloalkoxy, S(0),CI-C2-haloalkyl or halogen,
 15 R15 in each case independently of one another represent hydrogen or represent in each case optionally substituted C,-C6-haloalkyl or C,-C6-alkyl, where the substituent independently of one another may be selected from the group consisting of cyano, C,-C4-alkoxy, CI-C4- haloalkoxy, C,-C4-alkylthio, C,-C4-alkylsulfinyl, C,-C4-alkylsulfonyl, C,-C4-haloalkylthio, C,-C4-haloalkylsulfinyl or C,-C4-haloalkylsulfonyl,
    20    R18    in each case represents hydrogen or C,-C4-alkyl,
R19    in each case independently of one another represent hydrogen or CI-C6-alkyl,
p    independently of one another represents 0, 1, 2.
In the radical definitions mentioned as being preferred, halogen represents fluorine, chlorine, bromine
    25    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
R2    represents hydrogen or methyl,
    30    R3    represents C,-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,
 
- 7 -
R7    represents chlorine or bromine,
R9    represents trifluoromethyl, chlorine, bromine, difluoromethoxy or trifluoroethoxy.
Very particular preference is given to active compound combinations comprising the following 5    compounds of the formula (I-1):
 
Example No.    R2    R3    R4    R5    R7    R9    m.p• (°C)
I-1-1        Me    Me    Cl    Cl    CF3    185-186
1-1-2        Me    Me    Cl    Cl    OCH2CF3    :-207-208
1-1-3        Me    Me    Cl    Cl    CI    225-226
1-1-4        Me    Me    Cl    Cl    Br    162-164
1-1-5        Me    Cl    Cl    Cl    CF3    155-157
1-1-6        Me    Cl    Cl    Cl    OCH2CF3    192-195
1-1-7        Me    Cl    Cl    Cl    CI    205-206
1-1-8        Me    Cl    Cl    Cl    Br    245-246
1-1-9        i-Pr    Me    Cl    Cl    CF3    195-196
1-1-10        i-Pr    Me    CI    Cl    OCH2CF3    217-218
I-1-11        i-Pr    Me    Cl    Cl    Cl    173-175
1-1-12        i-Pr    Me    Cl    Cl    Br    159-161
I-1-13        i-Pr    Cl    Cl    Cl    CF3    200-201
1-1-14        i-Pr    Cl    Cl    Cl    OCH2CF3    232-235
1-1-15        i-Pr    Cl    Cl    Cl    Cl    197-199
1-1-16        i-Pr    Cl    Cl    Cl    Br    188-190
1-1-17        Et    Me    CI    CI    CF3    163-164
1-1-18        Et    Me    Cl    Cl    OCH2CF3    205-207.
1-1-19        Et    Me    Cl    Cl    CI    199-200
1-1-20        Et    Me    Cl    Cl    Br    194-195
1-1-21        Et    Cl    Cl    CI    CF3    201-202
I-1-22        Et    Cl    CI    Cl    Cl    206-208
1-1-23        Et    Cl    Cl    Cl    Br    214-215
1-1-24        t-Bu    Me    Cl    CI    CF3    223-225
1-1-25        t-Bu    Me    Cl    Cl    Cl    163-165
1-1-26        t-Bu    Me    Cl    Cl    Br    159-161
1-1-27        t-Bu    Cl    CI    Cl    CF3    170-172
1-1-28        t-Bu    Cl    Cl    Cl    CI    172-173
1-1-29        t-Bu    Cl    Cl    Cl    Br    179-180
1-1-30        Me    Me    Br    Cl    CF3    222-223
1-1-31        Et    Me    Br    CI    CF3    192-193
1-1-32        i-Pr    Me    Br    Cl    CF3    197-198
 
                    -8-        
Example No.    R2    R3    R4    R5    R7    R9    m.p. (°C)
I-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
1-1-36    H    i-Pr    Me    Br    CI    Cl    152-153
1-1-37    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    CI    Br    194-196
1-1-40    H    i-Pr    Me    Br    CI    Br    185-187
1-1-41    H    t-Bu    Me    Br    Cl    Br    215-221
1-1-42    H    Me    Me    I    Cl    CF3    199-200
I-1-43    H    Et    Me    I    Cl    CF3    199-200
1-1-44    H    i-Pr    Me    I    Cl    CF3    188-189
1-1-45    H    t-Bu    Me    I    Cl    CF3    242-243
1-1-46    H    Me    Me    I    Cl    Cl    233-234
1-1-47    _..
c_
—    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    CI    CF3    162-163
1-1-53    H    Et    Br    Br    CI    CF3    188-189
1-1-54    H    i-Pr    Br    Br    CI    CF3    192-193
1-1-55    H    t-Bu    Br    Br    CI    CF3    246-247
1-1-56    H    Me    Br    Br    Cl    CI    188-190
1-1-57    H    Et    Br    Br    Cl    CI    192-194
1-1-58    H    i-Pr    Br    . Br    CI    Cl    197-199
1-1-59    H    t-Bu    Br    Br    CI    Cl    210-212
I4-60    H    Me    Br    Br    CI    Br    166-168
14 -61    H    Et    Br    Br    Cl    Br    196-197
1-1-62    H    i-Pr    Br    Br    CI    Br    162-163
1-1-63    H    t-Bu.    Br    Br    Cl    Br    194-196
1-1-64    H    t-Bu    Cl    Br    CI    CF3    143-145
1-1-65    Me    Me    Br    Br    Cl    CI    153-155
1-1-66    Me    Me    Me    Br    Cl    CF3    207-208
14 -67    Me    Me    CI    CI    CI    Cl    231-232
1-1-68    Me    Me    Br    Br    CI    Br    189-190
I-1-69    Me    Me    Cl    CI    CI    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

Especially preferred are active compound combinations comprising .a compound of the formulae below
 

 

 

 

 
Pyrethroids are known active compounds having insecticidal and acaricidal properties. Preference is given to active compound combinations according to the invention which, preferably, compriie the following pyrethroids (active compounds of group 2):
10    (2-1) acrinathrin (known from EP-A 0 048 186)
CF3 0
F3C---(0
H3
15    and/or
(2-3) betacyfluthrin (known from EP-A 0 206 149)
 
-14-
H3C
 
and/or
(2-4) cyhalothrin (known from DE-A 28 02 962)
CF3
5    and/or
(2-5) cyprmethrin (known from DE-A-2 326 077) CI
 
, and/or
(2-6) deltamethrin (known from DE-A 23 26 077)
10     

and/or
15    (2-8) ethofenprox (known from DE-A 31 17 510)
 

 
and/or
(2-9) fenpropathrin (known from DE-A 22 31 312)
 
- 15 -
 
and/or
(2-10) fenvalerate (known from DE-A 23 35 347)
CI
5 and/or
(2-11) flucythrinate (known from DE-A 27 57 066)
CN
and/or
(2-12) lambda-cyhalothrin (known from EP-A 0 106 469)
H3 0
10     

and/or
and/or
15    (2-14) taufluvalinate (known from EP-A 0 038 617)
 
CN
10    and/or
(2-19) cycloprothrin (known from DE-A 26 53 189)
ocH2cH3
and/or
(2-21) fubfenprox (known from DE-A 37 08 231)
 
- 17 -
 
(2-22) pyrethrin (known from The Pesticide Manual, 1997, 1 1 th edition, p. 1056)
 

 
R2° = -CH3 or -CO2CH3
R2' = -CH=CH2 or -CH3 or -CH2CH3
 

 
Particularly preferably, the active compound combinations according to the invention comprise at least one pyrethroid of group 2 selected from
(2-1) acrinathrin
15    (2-3) betacyfluthrin.
(2-5) cypermethrin.
(2-6) deltamethrin.
(2-12) lambda-cyhalothrin.
(2-14) taufluvalinate.
20 (2-24) gamma-cyhalothrin.
Especially preferred are active compound combinations comprising the compound of the formula (I-1-9) and a pyrethroid of group 2 selected from the compounds (2-1) to (2-24).
Especially preferred are active compound combinations comprising the compound of the formula 25    (I-1-11) and a pyrethroid of group 2 selected from the compounds (2-1) to (2-24).
Especially preferred are active compound combinations comprising the compound of the formula (11-12) and a pyrethroid of group 2 selected from the compounds (2-1) to (2-24).
 
- 18 -
Emphasis is given to the following specifically mentioned active compound combinations (2-component mixtures) comprising a compound of the formula (I-I) and a pyrethroid of group 2:
No.    Active compound combination comprising    No.    Active compound combination comprising
la)    (I-1-1) and (2-1) acrinathrin    28a)    (I-1-39) and (2-1) acrinathrin
lb)    (I-1-I) and (2-3) betacyfluthrin    28b)    (I-1-39) and (2-3) betacyfluthrin
1c)    (I-1-1) and (2-5) cypermethrin    28c)    (1-1-39) and (2-5) cypermethrin
1d)    (I-1-1) and (2-6) deltamethrin    28d)    (I-1-39) and (2-6) deltamethrin
le)    (I-1-1) and (2-12) lambda-cyhalothrin    28e)    (I-1-39) and (2-12) lambda-cyhalothrin
if)    (I-1-1) and (2-14) taufluvalinate    28f)    (I-1-39) and (2-14) taufluvalinate
1g)    (I-1-1) and (2-24) gamma-cyhalothrin    28g)    (I-1-39) and (2-24) gamma-cyhalothrin
2a)        (1-1-2) and (2-1) acrinathrin    29a)    (1-1-40) and (2-1) acrinathrin
2b)     2c)    (I-1-2) and (2-3) betacyfluthrin
th
    t(I-1-) an-    cypermethrin
2    (2-5) and (2    29b)
29c)    (I-1-40) and (2-3) betacyfluthrin
(I-1-40) and (2-5) cypermethrin
2d)    (I-1-2) and (2-6) deltamethrin    29d)    (I-1-40) and (2-6) deltamethrin
2e)    (I-1-2) and (2-12) lambda-cyhalothrin    29e)    (I-1-40) and (2-12) lambda-cyhalothrin
2f)    (I-1-2) and (2-14) taufluvalinate    29f)    (I-1-40) and (2-14) taufluvalinate
2g)    (I-1-2) and (2-24) gamma-cyhalothrin    29g)    (I-1-40) and (2-24) gamma-cyhalothrin
3a)    (I-1-3) and (2-1) acrinathrin    30a)    (1-1-42) and (2-1) acrinathrin
3b)    (I-1-3) and (2-3) betacyfluthrin    30b)    (1-1-42) and (2-3) betacyfluthrin
3c)    (I-1-3) and (2-5) cypermethrin    30c)    (I-1-42) and (2-5) cypermethrin
3d)    (I-1-3) and (2-6) deltamethrin    30d)    (I-1-42) and (2-6) deltamethrin
3e)    (I-1-3) and (2-12) lambda-cyhalothrin    30e)    (I-1-42) and (2-12) lambda-cyhalothrin
3f)    (I-1-3) and (2-14) taufluvalinate    30f)    (I-1-42) and (2-14) taufluvalinate
3g)    (I-1-3) and (2-24) gamma-cyhalothrin    30g)    (1-1-42) and (2-24) gamma-cyhalothrin
4a)    (I-1-4) and (2-1) acrinathrin    3 I a)    (I-1-43) and (2-1) acrinathrin
4b)    '    (I-1-4) and (2-3) betacyfluthrin    31b)    (1-1-43) and (2-3) betacyfluthrin
4c)    (I-1-4) and (2-5) cypermethrin    31c)    (1-1-43) and (2-5) cypermethrin
4d)    (I-1-4) and (2-6) deltamethrin    31d)    (I-1-43) and (2-6) deltamethrin
4e)    (I-1-4) and (2-12) lambda-cyhalothrin    31e)    (I-1-43) and (2-12) lambda-cyhalothrin
4f)    (I-1-4) and (2-14) taufluvalinate    310    (I-1-43) and (2-14) taufluvalinate
4g)    (I-1-4) and (2-24) gamma-cyhalothrin    31g)    (1-1-43) and (2-24) gamma-cyhalothrin
5a)    (I-1-5) and (2-1) acrinathrin    32a)    (I-1-44) and (2-1) acrinathrin
5b)    (I-1-5) and (2-3) betacyfluthrin    32b)    (I-1-44) and (2-3) betacyfluthrin
5c)    (I-1-5) and (2-5) cypermethrin    32c)    (1-1-44) and (2-5) cypermethrin
5d)    (1-1-5) and (2-6) deltamethrin    32d)    (I-1-44)" and (2-6) deltamethrin
5e)    (I-1-5) and (2-12) lambda-cyhalothrin     32e)    (I-1-44) and (2-12) lambda-cyhalothrin
5f)    (I-1-5) and (2-14) taufluvalinate    32f)    (1-1-44) and (2-14) taufluvalinate
5g)    (I-1-5) and (2-24) gamma-cyhalothrin    32g)    (1-1-44) and (2-24) gamma-cyhalothrin
6a)    (I-1-6) and (2-1) acrinathrin    _    33a)    (I-1-50) and (2-1) acrinathrin
 
-19-
No.    Active compound combination comprising    No.    Active compound combination comprising
6b)    (I-1-6) and (2-3) betacyfluthrin    33b)    (I-1-50) and (2-3) betacyfluthrin
6c)    (I-1-6) and (2-5) cypermethrin    33c)    (I-1-50) and (2-5) cypermethrin
6d)    (I-1-6) and (2-6) deltamethrin    33d)    (I-1-50) and (2-6) deltamethrin
6e)    (I-1-6) and (2-12) lambda-cyhalothrin    33e)        (I-1-50) and (2-12) lambda-cyhalothrin
60    (I-1-6) and (2-14) taufluvalinate    33f)        (I-1-50) and (2-14) taufluvalinate
6g)    (I-1-6) and (2-24) gamma-cyhalothrin    33g)        (I-1-50) and (2-24) gamma-cyhalothrin
7a)    (I-1-7) and (2-1) acrinathrin    34a)    (I-1-51) and (2-1) acrinathrin
7b)    (I-1-7) and (2-3) betacyfluthrin    34b)    (I-1-51) and (2-3) betacyfluthrin
7c)    (I-1-7) and (2-5) cypermethrin    34c)    (I-1-51) and (2-5) cypermethrin
7d)    (I-1-7) and (2-6) deltamethrin    34d)    (I-1-51) and (2-6) deltamethrin
7e)    (I-1-7) and (2-12) lambda-cyhalothrin    34e)    (I-1-51) and (2-12) lambda-cyhalothrin
7f)    (I-1-7) and (2-14) taufluvalinate    34f)    (I-1-51) and (2-14) taufluvalinate
7g)    (I-/-7). and (2-24) gamma-cyhalothrin    34g)    (I-1-51) and (2-24) gamma-cyhalothrin
8a)    (I-1-8) and (2-1) acrinathrin    35a)    (I-1-52jand (2-1) acrinathrin
8b)    (I-1-8) and (2-3) betacyfluthrin    35b)    (1-1-52) and (2-3) betacyfluthrin
8c)    (I-1-8) and (2-5) cypermethrin    35c)    (I-1-52) and (2-5) cypermethrin
8d)    (I-1-8) and (2-6) deltamethrin    35d)    (I-1-52) and (2-6) deltamethrin
8e)    (I-1-8) and (2-12) lambda-cyhalothrin    35e)        (I-1-52) and (2-12) lambda-cyhalothrin
80    (I-1-8) and (2-14) taufluvalinate    35f)        (1-1-52) and (2-14) taufluvalinate
8g)    (I-1-8) and (2-24) gamma-cyhalothrin    35g)        (1-1-52) and (2-24) gamma-cyhalothrin
9a)    (I-1-9) and (2-1) acrinathrin    36a)    (1-1-53) and (2-1) acrinathrin
9b)    (I-1-9) and (2-3) betacyfluthrin    36b)    (I-1-53) and (2-3) betacyfluthrin
9c)    (I-1-9) and (2-5) cypermethrin    36c)    (I-1-53) and (2-5) cypermethrin
9d)    (I-1-9) and (2-6) deltamethrin    36d)    (1-1-53) and (2-6) deltamethrin
9e)    (I-1-9) and (2-12) lambda-cyhalothrin    36e)    (1-1-53) and (2-12) lambda-cyhalothrin
9f)    (I-1-9) and (2-14) taufluvalinate    36f)    (I-1-53) and (2-14) taufluvalinate
9g)    (I-1-9) and (2-24) gamma-cyhalothrin    36g)    (I-1-53) and (2-24) gamma-cyhalothrin
10a)    (I-1-11) and (2-1) acrinathrin    37a)    (I-1-54) and (2-1) acrinathrin
10b)    (I-1-11) and (2-3) betacyfluthrin    37b)    (I-1-54) and (2-3) betacyfluthrin
10c)    (I-1-11) and (2-5) cypermethrin    37c)    (1-1-54) and (2-5) cypermethrin
10d)    (I-1-11) and (2-6) deltamethrin    37d)    (1-1-54) and (2-6) deltamethrin
10e)    (I-1-11) and (2-12) lambda-cyhalothrin    37e)    (I-1-54) and (2-12) lambda-cyhalothrin
10f)    (I-1-11) and (2-14) taufluvalinate    371)    (1-1-54) and (2-14) taufluvalinate
10g)    (I-1-11) and (2-24) gamma-cyhalothrin    37g)    (I-1-54) and (2-24) gamma-cyhalothrin
1 I a)    (I-1-12) and (2-1) acrinathrin    38a)    (1-1-55) and (2-1) acrinathrin
11b)    (I- 1 - 1 2) and (2-3) betacyfluthrin    38b)    (1-1-55) and (2-3) betacyfluthrin
11e)    (I-1-12) and (2-5) cypermethrin    38c)    (I-1-55) and (2-5) cypermethrin
11d)    (I-1-12) and (2-6) deltamethrin    38d)    (I-1-55) and (2-6) deltamethrin
11e)    (I-1-12) and (2-12) lambda-cyhalothrin    38e)    (I-1-55) and (2-12) lambda-cyhalothrin
110    (I-1-12) and (2-14) taufluvalinate    38f)    (I-1-55) and (2-14) taufluvalinate
 
-20-
No.    Active compound combination comprising    No.    Active compound combination comprising
11g)    (I-1-12) and (2-24) gamma-cyhalothrin    38g)    (I-1-55) and (2-24) gamma-cyhalothrin
12a)    (I-1-13) and (2-1) acrinathrin    39a)    (I-1-56) and (2-1) acrinathrin
12b)    (I-1-13) and (2-3) betacyfluthrin    39b)    (I-1-56) and (2-3) betacyfluthrin
12c)    (I-1-13) and (2-5) cypermethrin    39c)    (1-1-56) and (2-5) cypermethrin
12d)    (I-1-13) and (2-6) deltamethrin    39d)    (1-1-56) and (2-6) deltamethrin
12e)    (1-1-13) and (2-12) lambda-cyhalothrin    39e)    (1-1-56) and (2-12) lambda-cyhalothrin
120    (I-1-13) and (2-14) taufluvalinate    391)    (I-1-56) and (2-14) taufluvalinate
12g)    (I-1-13) and (2-24) gamma-cyhalothrin    39g)    (I-1-56) and (2-24) gamma-cyhalothrin
13a)    (I-1-15) and (2-1) acrinathrin    40a)    (I-1-57) and (2-1) acrinathrin
13b)    (I-1-15) and (2-3) betacyfluthrin    40b)    (1-1-57) and (2-3) betacyfluthrin
13c)    (I-1-15) and (2-5) cypermethrin    40c)    (1-1-57) and (2-5) cypermethrin
13d)    (I-1-15) and (2-6) deltamethrin    40d)    (1-1-57) and (2-6) deltamethrin
13e)    (I-L-15) and (2-12) lambda-cyhalothrin    40e)        (I-1-57) and (2-12) lambda-cyhalothrin
131)    (r1-15) and (2-14) taufluvalinate    40f)        (I-1-57rald (2-14) taufluvalinate
13g)    (1-1-15) and (2-24) gamma-cyhalothrin    40g)        (I-1-57) and (2-24) gamma-cyhalothrin
14a)    (I-1-16) and (2-1) acrinathrin    41a)    , (I-1-58) and (2-1) acrinathrin    -
14b)    (I-1-16) and (2-3) betacyfluthrin    41b)    (I-1-58) and (2-3) betacyfluthrin
14c)    (I-1-16) and (2-5) cypermethrin    41c)    (1-1-58) and (2-5) cypermethrin
14d)    (I-1-16) and (2-6) deltamethrin    41d)    (I-1-58) and (2-6) deltamethrin
14e)    (I-1-16) and (2-12) lambda-cyhalothrin    41e)        (I-1-58) and (2-12) lambda-cyhalothrin
141)    (I-1-16) and (2-14) taufluvalinate    41f)        (I-1-58) and (2-14) taufluvalinate
14g)    (I-1-16) and (2-24) gamma-cyhalothrin    41g)        (1-1-58) and (2-24) gamma-cyhalothrin
15a)    (1-1-19) and (2-1) acrinathrin    42a)    (1-1-60) and (2-1) acrinathrin
15b)    (I-1-19) and (2-3) betacyfluthrin    42b)    (I-1-60) and (2-3) betacyfluthrin
15c)    (I-1-19) and (2-5) cypermethrin    42c)    (I-1-60) and (2-5) cypermethrin
15d)    ,    (I-1-19) and (2-6) deltamethrin    42d)    (I-1-60) and (2-6) deltamethrin
15e)    (I-1-19) and (2-12) lambda-cyhalothrin    42e)    (I-1-60) and (2-12) lambda-cyhalothrin
15f)    (I-1-19) and (2-14) taufluvalin ate    42f)    (I-1-60) and (2-14) taufluvalinate
15g)    (1-1-19) and (2-24) gamma-cyhalothrin    42g)    (I-1-60) and (2-24) gamma-cyhalothrin
16a)    (I-1-21) and (2-1) acrinathrin    43a)    (I-1-61) and (2-1) acrinathrin
16b)    (I-1-21) and (2-3) betacyfluthrin    '    43 b)    (I-1-61) and (2-3) betacyfluthrin
16c)    (I-1-21) and (2-5) cypermethrin    43c)    (I-1-61) and (2-5) cypermethrin
16d)    (I-1-21) and (2-6) deltamethrin    43d)    (I-1-61) and (2-6) deltamethrin
16e)    (I-1-21) and (2-12) lambda-cyhalothrin    43e)        (I-1-61) and (2-12) lambda-cyhalothrin
160    (I-1-21) and (2-14) taufluvalinate    43f)        (1-1-61) and (2-14) taufluvalinate
16g)    (I-1-21) and (2-24) gamma-cyhalothrin    . 43g)    (I-1-61) and (2-24) gamma-cyhalothrin
17a)    (I-1-22) and (2-1) acrinathrin    44a)    (I-1-62) and (2-1) acrinathrin
17b)     (I-1-22) and (2-3) betacyfluthrin    44b)    (1-1-62) and (2-3) betacyfluthrin
17c)    (I-1-22) and (2-5) cypermethrin    44c)    (1-1-62) and (2-5) cypermethrin
17d)    (1-1-22) and (2-6) deltamethrin    44d)    (1-1-62) and (2-6) deltamethrin
 
- 21 -

No.    Active compound combination comprising    No.    Active compound combination comprising
17e)    (1-1-22) and (2-12) lambda-cyhalothrin    44e)    (1-1-62) and (2-12) lambda-cyhalothrin
17f)    (1-1-22) and (2-14) taufluvalinate    44f)    (I-1-62) and (2-14) taufluvalinate
17g)    (I-1-22) and (2-24) gamma-cyhalothrin    44g)    (I-1-62) and (2-24) gamma-cyhalothrin
18a)    (1-1-23) and (2-1) acrinathrin    45a)    (I-1-64) and (2-1) acrinathrin
18b)    (I-1-23) and (2-3) betacyfluthrin    45b)    (1-1-64) and (2-3) betacyfluthrin
18c)    (I-1-23) and (2-5) cypermethrin    45c)    (I-1-64) and (2-5) cypermethrin
18d)    (I-1-23) and (2-6) deltamethrin    45d)    (1-1-64) and (2-6) deltamethrin
18e)    (I-1-23) and (2-12) lambda-cyhalothrin    45e)    (I-1-64) and (2-12) lambda-cyhalothrin
18f)    (I-1-23) and (2-14) taufluvalinate    45f)    (I-1-64) and (2-14) taufluvalinate
18g)    (1-1-23) and (2-24) gamma-cyhalothrin    45g)    (1-1-64) and (2-24) gamma-cyhalothrin
19a)    (1-1-24) and (2-1) acrinathrin    46a)    (1-1-65) and (2-1) acrinathrin
19b)    (I-1-24) and (2-3) betacyfluthrin    46b)    (1-1-65) and (2-3) betacyfluthrin
19c)    JI-1-24) and (2-5) cypermethrin    46c)    (1-1-65) and (2-5) cypermethrin
19d)    (-1-24) and (2-6) deltamethrin    46d)    (I-1-61ra nd (2-6) deltamethrin
19e)    (I-1-24) and (2-12) lambda-cyhalothrin    46e)        (I-1-65) and (2-12) lambda-cyhalothrin
190    (I-1-24) and (2-14) taufluvalinate    46f)        (1-1-65) and (2-14) taufluvalinate
19g)    (I-1-24) and (2-24) gamma-cyhalothrin    46g)        (1-1-65) and (2-24) gamma-cyhalothrin
20a)    (I-1-26) and (2-1) acrinathrin    47a)    (1-1-66) and (2-1) acrinathrin
20b)    (I-1-26) and (2-3) betacyfluthrin    47b)    (1-1-66) and (2-3) betacyfluthrin
20c)    (I-1-26) and (2-5) cypermethrin    47c)    (I-1-66) and (2-5) cypermethrin
20d)    (I-1-26) and (2-6) deltamethrin    47d)    (1-1-66) and (2-6) deltamethrin
20e)    (I-1-26) and (2-12) lambda-cyhalothrin    47e)    (I-1-66) and (2-12) lambda-cyhalothr in
20f)    (I-1-26) and (2-14) taufluvalinate    47f)    (1-1-66) and (2-14) taufluvalinate
20g)    (I-1-26) and (2-24) gamma-cyhalothrin    47g)    (1-1-66) and (2-24) gamma-cyhalothrin
21a)    (I-1-27) and (2-1) acrinathrin    48a)    (I-1-67) and (2-1) acrinathrin
21b)    (I-1-27) and (2-3) betacyfluthrin    48b)    (1-1-67) and (2-3) betacyfluthrin
21c)    (1-1-27) and (2-5) cypermethrin    48c)    (1-1-67) and (2-5) cypermethrin
21d)    (I-1-27) and (2-6) deltamethrin    48d)    (1-1-67) and (2-6) deltamethrin
21e)    (I-1-27) and (2-12) lambda-cyhalothrin    48e)    (I-1-67) and (2-12) lambda-cyhalothrin
21f)    (I-1-27) and (2-14) taufluvalinate    480    (I-1-67) and (2-14) taufluvalinate
21g)    (I-1-27) and (2-24) gamma-cyhalothrin    48g)    (I-1-67) and (2-24) gamma-cyhalothrin
22a)    (I-1-29) and (2-1) acrinathrin    49a)    (I-1-68) and (2-1) acrinathrin
22b)    (1-1-29) and (2-3) betacyfluthrin    49b)    (I-1-68) and (2-3) betacyfluthrin    .
22c)    (I-1-29) and (2-5) cypermethrin    49c)    (1-1-68) and (2-5) cypermethrin
22d)    (1-1-29) and (2-6) deltamethrin    49d)    (1-1-68) and (2-6) 'deltamethrin
22e)    (I-1-29) and (2-12) lambda-cyhalothrin    49e)    (I-1-68) and (2-12) lambda-cyhalothrin
22f)    (I-1-29) and (2-14) taufluvalinate    490    (I-1-68) and (2-14) taufluvalinate
22g)    (I-1-29) and (2-24) gamma-cyhalothrin    49g)    (1-1-68) and (2-24) gamma-cyhalothrin
23a)    (1-1-30) and (2-1) acrinathrin    50a)    (I-1-69) and (2-1) acrinathrin
23b)    (I-1-30) and (2-3) betacyfluthrin    50b)    (1-1-69) and (2-3) betacyfluthrin
 
- 22 -
 
Active compound combination comprising
(I-1-30) and (2-5) cypermethrin
(I-1-30) and (2-6) deltamethrin
(I-1-30) and (2-12) lambda-cyhalothrin
(I-1-30) and (2-14) taufluvalinate
(I-1-30) and (2-24) gamma-cyhalothrin
(I-1-31) and (2-1) acrinathrin
(I-1-31) and (2-3) betacyfluthrin
(1-1-31) and (2-5) cypermethrin
(I-1-31) and (2-6) deltamethrin
(I-1-31) and (2-12) lambda-cyhalothrin
(I-1-31) and (2-14) taufluvalinate
(I-1-31) and (2-24) gamma-cyhalothrin
(I-.1-32) and (2-1) acrinathrin
(1--1-32) and (2-3) betacyfluthrin
(1-1-32) and (2-5) cypermethrin
(1-1-32) and (2-6) deltamethrin
(I-1-32) and (2-12) lambda-cyhalothrin
(I-1-32) and (2-14) taufluvalinate
(1-1-32) and (2-24) gamma-cyhalothrin
(I-1-33) and (2-1) acrinathrin
(I-1-33) and (2-3) betacyfluthrin
(1-1-33) and (2-5) cypermethrin
(I-1-33) and (2-6) deltamethrin
(I-1-33) and (2-12) lam bda-cyhalothrin
(I-1-33) and (2-14) taufluvalinate
(1-1-33) and (2-24) gamma-cyhalothrin
(I-1-38) and (2-1) acrinathrin
(I-1-38) and (2-3) betacyfluthrin
(1-1-38) and (2-5) cypermethrin
(1-1-38) and (2-6) deltamethrin
(I-1-38) and (2-12) lambda-cyhalothrin
(I-1-38) and (2-14) taufluvalinate
(I-1-38) and (2-24) gamma-cyhalothrin
 
However, the general or preferred radical definitions or illustrations listed above can also be combined with one another as desired, i.e. between their respective ranges and preferred ranges. The definitions apply to the end products and, correspondingly, to precursors and intermediates.
 
- 23 -
Preference according to the invention is given to active compound combinations comprising compounds of the formula (1) and pyrethroids of the formulae (2-1) to (2-24), where the 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
    5    comprising compounds of the formula (1) and pyrethroids of the formulae (2-1) to (2-24), where the
individual radicals are a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to active compound combinations
comprising compounds of the formula (1) and pyrethroids of the formulae (2-1) to (2-24), where the
    10    individual radicals are a combination of the meanings listed above as being very particularly
preferred.
Saturated eir 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
    15    example, in alkoxy.
Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different.
    20    In addition, the active compound combinations may also comprise further fungicidally, acaricidally or
insecticidally active additives.
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. However, the weight ratios
 25 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 comprise active compounds of the formula (I) and the mixing partner of the group 2 in the preferred and particularly preferred mixing ratios given:
    30    the mixing ratios are based on weight ratios. The ratio is to be understood as meaning
active compound of the formula (1):mixing partner
Mixing partner    Preferred mixing ratio    Particularly preferred mixing ratio
Acrinathrin    20:1 to 1:50    10:1 to 1:1
Alpha-Cypermethrin    50:1 to 1:5    10:1 to 1:1
Betacyfluthrin    50:1 to 1:5    10:1 to 1:1
 
- 24 -
Mixing partner    Preferred mixing ratio    Particularly preferred mixing ratio
cyhalothrin    50:1 to 1:5    10:1 to 1:1
cypermethrin    50:1 to 1:5    10:1 to 1:1
deltamethrin    50:1 to 1:5    10:1 to 1:1
esfenvalerate    50:1 to 1:5    10:1 to 1:1
etofenprox    10:1 to 1:10    5:1 to 1:5
fenpropathrin    10:1 to 1:10    5:1 to 1:5
fenvalerate    20:1 to 1:5    10:1 to 1:1
flucythrinate    50:1 to 1:5    10:1 to 1:1
lambda-cyhalothrin    50:1 to 1:5    10:1 to 1:1
permethrin    10:1 to 1:10    5:1 to 1:5
tau-fluvalinate    20:1 to 1:5    10:1 to 1:2
tralomethril1/2-    50:1 to 1:5    -    10:1 to 1:1
zeta-cypermethrin    50:1 to 1:5    10:1 to 1:2
cyfluthrin    50:1 to 1:5    10:1 to 1:1
bifenthrin    10:1 to 1:10    10:1 to 1:1
cycloprothrin    10:1 to 1:10    5:1 to 1:5
eflusilanate    10:1 to 1:10    5:1 to 1:5
fubfenprox    10:1 to 1:10    5:1 to 1:5
pyrethrin    50:1 to 1:10    5:1 to 1:1
resmethrin     50:1 to 1:10    5:1 to 1:1
gamma-cyhalothrin    50:1 to 1:5    1Q:1 to 1:1

The active compound combinations according to 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
5        sector. 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.
10        From the order of the Chilopoda, for example, Geophilus carpophagus, Scutigera spp.
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.
 
- 25 -
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, Frankliniella occidentalis.
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the or—der 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.
 
-26-
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., Hemitirsonemus 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.
 
-27-
Suitable solid carriers are:
for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz,
attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as highly
disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and
 5 fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn 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,
    10    or else protein hydrolysates; suitable dispersants are: for example lignosulfite waste liquors and
methylcellulose.
Tackifiers much 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
    15    natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the
formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and
I
Prussian Blue, and organic colorants such as alizarin colorants, azo colorants and metal
    20    phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
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 according to 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
    30    example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and
substances produced by microorganisms, inter alia.
Mixtures with other known active compounds such as herbicides or with fertilizers and growth regulators are also possible.
 
- 28 -
When used as insecticides, the active compound combinations according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these 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.
5
The active compound content of the use forms prepared from the commercially available 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.
10 The compounds are employed in a customary manner appropriate for the use forms.
When used against hygiene pests and stored-product pests, the active compound combinations are distinguislied by an excellent residual action on wood and clay as well as good stability to alkali on limed substrates.
15
The active compound combinations according to the invention are not only active against plant pests, hygiene 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:
20  From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Ttimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
25    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., 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
30  spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
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., 35    Panstrongylus spp.
 
- 29 -
From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattella germanica, Supella spp.
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.,
5 Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.
From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis
spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,
Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes
10        spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres
spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
The active compound combinations according to the invention are also suitable for controlling
arthropods which attack agricultural livestock such as, for example, cattle, sheep, goats, horses, pigs,
15 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, 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
20    of the active compound combinations according to the invention.
The active compound combinations according to 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
25 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, 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.
30
When used for cattle, poultry, domestic animals and the like, the active compound combinations can 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.
 
- 30 -
Moreover, it has been found that the active compound combinations according to the invention show a potent insecticidal action against insects which destroy industrial materials.
The following insects may be mentioned by way of example and with preference, but not by way of
    5    limitation:
Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus
    10    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 flavipes, Reticulitermes santonensis, Reticulitermes lucifugus,_ Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
    15    Bristle-tails such as Lepisma saccharina.
Industrial materials in the present context are understood as meaning non-living materials such as, preferably, polymers, adhesives, glues, paper and board, leather, wood, timber products and paints.
    20    The material which is to be protected from insect attack is very particularly preferably wood and
timber products.
Wood and timber products which can be protected by the composition according to the invention, or mixtures comprising it, are to be understood as meaning, for example:
    25    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 or building joinery.
    30    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.
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
    35    fixative, water repellant, if desired desiccants and UV stabilizers, and if desired colorants and
pigments and other processing auxiliaries.
 
-31-
The insecticidal compositions or concentrates used for protecting wood and timber products comprise the active compound according to 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
10    protected.
A suitable solvent and/or diluent is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical °chemical 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
20    white spirit, petroleum and/or alkylbenzene.
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.
30    The organic oily or oil-type solvents of low volatility and with an evaporation number of above 35
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.
 
- 32 -
In a preferred embodiment, some of the organochemical solvent or solvent mixture or an aliphatic polar organochemical solvent or solvent mixture is replaced. Aliphatic organochemical solvents which contain hydroxyl and/or ester and/or ether groups are preferably used, such as, for example, glycol ethers, esters or the like.
5
Organochemical binders used for the purposes of the present invention are the synthetic resins and/or 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,
10 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 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
15 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 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
20 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 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
25 (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 binder employed).
The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl
30 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, 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, 35    or ketones such as benzophenone and ethylenebenzophenone.
 
- 33 -
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.
Particularly effective timber protection is achieved by industrial-scale impregnating processes, for 5    example the vacuum, double-vacuum or pressure processes.
The active compound combinations according to the invention can equally be employed for protecting objects which come into contact with saltwater or brackish water, in particular hulls, screens, nets, buildings, quaysides and signaling systems, against fouling.
10
Fouling by sessile Oligochaeta, such as Serpulidae, and by shells and species from the Ledamorpha group (goose barnacles), such as various Lepas and Scalpellum species, or by species from the Balanomorgh a 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
15    energy consumption and additionally frequent stops in the dry dock.
Apart from fouling by algae, for example Ectocarpus sp. and Ceramium sp., in particular fouling by sessile Entomostraka groups, which come under the generic term Cirripedia (cirriped crustaceans), is of particular importance.
20
Surprisingly, it has now been found that the active compound combinations according to the invention have an outstanding antifouling action.
Use of the active compound combinations according to the invention allows the use of heavy metals
25 such as, for example, in bis(trialkyltin) sulfides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride, tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenum 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, bisdimethyl-
30 dithiocarbamoylzinc ethylenebisthiocarbamate, zinc oxide, copper(1) ethylenebisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides to be dispensed 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, 35    preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.
 
- 34 -
Preferable suitable combination partners for the antifouling compositions according to the invention are:
algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophen, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and
    5    terbutryn;
fungicides such as benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynyl butylcarbamate, tolylfluanid and azoles such as azaconazole,
cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole; molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and
    10    trimethacarb;
or conventional antifouling active compounds such as 4,5-dichloro-2-octy1-4-isothiazolin-3-one, diiodomethylparatryl sulfone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium salts, copper saki, sodium salts and zinc salts of 2-pyridinethiol 1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, 2,4,5,6-tetrachloroisophthalo-
    15    nitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.
The antifouling compositions used comprise the active compound combinations according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
    20    Moreover, the antifouling compositions according to the invention comprise the customary
components such as, for example, those described in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
Besides the algicidal, fungicidal, molluscicidal active compounds and insecticidal active compounds
    25    according to the invention, antifouling paints comprise, in particular, binders.
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
 •30 solvent systems, butadiene/styrene/acrylonitrile rubbers, drying oils such as linseed oil, resin esters or modified hardened resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.
If appropriate, paints also comprise inorganic pigments, organic pigments or colorants which are
    35    preferably insoluble in seawater. 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 according to the invention or the abovementioned mixtures may also be incorporated into self-polishing antifouling systems.
    5    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, 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:
    10    From the order of the Scorpionidea, for example, Buthus occitanus.
From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicul alfreddugesi, Neutromb icu la autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
    15    From the order of the Araneae, for example, Aviculariidae, Araneidae.
From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones 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.
    20    From the order of the Chilopoda, for example, Geophilus spp.
From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta
    25    americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
From the order of the Saltatoria, for example, Acheta domesticus.
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.
    30    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 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
    35    pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp.,
Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
 
-36-
From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
    5    From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus,
Lasius niger, Lasius umbratus, Monomorium pharaonic, Paravespula spp., Tetramorium caespitum. 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, Rhodnius
    10    prolixus, Triatoma infestans.
They are used as aerosols, pressureless spray products, for example pump and atomizer sprays,
automatic egging systems, foggers, foams, gels, evaporator products with evaporator tablets made of
cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven
    15    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.
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
 20 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 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
 25 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 harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
    30    The treatment according to 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 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.
 
- 37 -
As already mentioned above, it is possible to treat all plants and their parts according to the invention. 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 further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering
 5 methods, 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.
Particularly preferably, plants of the plant cultivars which are in each case commercially available or
    10    in use are treated according to the invention.
Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate,
vegetation jeriod, diet), the treatment according to the invention may also result in superadditive
("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity
 15 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 value of the harvested products, better storage stability and/or processability of the
    20    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
modification, received genetic material which imparts particularly advantageous useful traits to these
 25 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 harvested products. Further and particularly emphasized examples of such properties are a better
 30 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), corn, soya beans, potatoes, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular
    35    emphasis is given to corn, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are
particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes
 
-38-
and slugs and snails by toxins formed in the plants, in particular those formed by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CrylEA, CryII1B2, 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
 5 the plants against fungi, bacteria and viruses by Systemic Acquired Resistance (SAR), systemin, phytoalexins, elicitors, as well as 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, sulfonylureas, glyphosate or phosphinotricin (for example the "PAT" gene). The genes in question which impart the desired traits
 10 can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are corn varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example corn, cotton, soya beans), KnockOut® (for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are
 15 corn varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example corn, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, for example corn). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name
    20    Clearfield® (for example corn). 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.
The plants listed can be treated according to the invention in a particularly advantageous manner
with the active compound mixtures according to the invention. The preferred ranges stated above
    25    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.
The good insecticidal and acaricidal action of the active compound combinations according to the invention can be seen from the examples which follow. While the individual active compounds show
    '30    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 compound combinations exceeds the total of the, actions of the active compounds when applied individually.
 
-39-
The expected action for a given combination of two active compounds can be calculated as follows, according to S.R. Colby, Weeds 15 (1967), 20-22:
If
5    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
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
10    compounds A and B at application rates of m and n g/ha or in a concentration of m and n
ppm,
then
X • Y
E=X Y— 100
15
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).
20    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.
 
-40-
Use examples
Example A
5 Myzus persicae test
Solvent:    7 parts by weight of dimethylformamide
Emulsifier:    2 parts by weight of alkylaryl polyglycol ether
10 To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed 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 15 — persicae) are treated by being dipped into the preparation of active compound of the desired concentration.
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 kill rates determined are calculated 20    using Colby's formula (see page 39).
In this test, for example, the following active compouna combination in accordance with the present application shows a synergistically enhanced activity compared to the active compounds applied on their own:
 
- 41 -
Table Al: Plant-damaging insects
Myzus persicae test
Active compounds    Concentration of active
compound in ppm    Kill rate after
found*    in % 6d
calc.**
H3C
H3C    0    NI /
CI     FIN    CI
`N
H3C O    /
CF3
(1-1-9)    4    15   
0    CN
    H3C    CH
B
    Br -.,    ®el
_
(2-6) deltamethrin    0.16
-    50   
(I-1-9) + (2-6) deltamethrin (25:1)    4 + 0.16    80    57.5

* found    = activity found
** calc.    = activity calculated using Colby's formula
Table A2: Plant-damaging insects
Myzus persicae test
Active compounds    Concentration of active
compound in ppm    Kill rate after
found*    in % 6d
calc.**
H3C
O    \
H3C
N    ..'
CI    H    CI
I .
H3C    ;
CF3
(1-1-9)    0.8    0   
H3    O
H3C    CN
O
CI
F3C    . .
(2-12) lambda-cyhalothrin    0.032    0
,   
(1-1-9) + (2-12) lambda-cyhalothrin (25:1)    0.8 + 0.032    45    0

* ' found    = activity found
** calc.    = activity calculated using Colby's formula
 
- 42 -
Example B
Phaedon cochleariae larvae test
5 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 with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-10    containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound•9f the desired concentration and are populated with larvae of the mustard beetle (Phaedon cochleariae) while the leaves are still moist.
15
After the desired period of time, the kill in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed. The kill rates determined are calculated using Colby's formula (see page 39).
20    In this test, the following active compound combination in accordance with the present application
showed a synergistically enhanced activity compared to the active compounds applied on their own:
 
- 43 -
Table B: Plant-damaging insects
Phaedon cochleariae larvae test

Active compounds    Concentration of active
compound in ppm    Kill rate after
found*    in % 3d
talc.**
H3C
"...
0
H3C
N    ..."
    CI • H    CI
    H3C O    /
CF3
(I-1-9)    0.16    0   
O    CH3    0.16    ----    15   
NC
....    O    CI
.._
4.    CI
F
(2-3) betracyfluthrin           
(I-1-9) + (2-3) betracyfluthrin (1:1)    0.16 + 0.16    35    15

    found    = activity found
    ** talc.    = activity calculated using Colby's formula
 
- 44 -
Example C
Plutella-xylostella test (resistant strain)
5 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 with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-10    containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compoundm_- f the desired concentration and are populated with caterpillars of the diamond back moth (Plutella xylostella, resistant strain), while the leaves are still moist.
15
After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed. The kill rates determined are calculated using Colby's formula (see page 39).
20    In this test, the following active compound combination in accordance with the present application
showed a synergistically enhanced activity compared to the active compounds applied on their own:
 
- 45 -
Table Cl: Plant-damaging insects
Plutella-xylostella test (resistant strain)
Active compounds    Concentration of active
compound in ppm    Kill rate after
found*    in % 6d
calc.**
H3C).---N
H3C    0
N /
CI . H    Cl
H3C O    /
CF3
(I- 1 -9)    0.0064    0   
cH3
0NC
O
lip    0)-\--tC(H,
11411    A    ...., CI
F    CI
(2-3) betracyfluthrin    0.0064    0   
(1-1-9) + (2-3) betracyfluthrin (1:1)    0.0064 + 0.0064    35    0

* found    = activity found
** calc.    = activity calculated using Colby's formula
Table C2: Plant-damaging insects
Plutella-xylostella test (resistant strain)
Active compounds    Concentration of active
compound in ppm    Kill rate after
found*    in % 6d
calc.**
H3C)--N
H3C    0
N
    it H    CI
CI 
    H3C O    /N
CF3
(1-1-9)    0.0064    10   
H3C    CN
O
CI    .
F3C    •
(2-12) lambda-cyhalothrin    0.0064    0   
(171-9) + (2-12) lambda-cyhalothrin (1:1)    0.0064 + 0.0064    1    45    10

* found    = activity found
** calc.    = activity calculated using Colby's formula
 
-46-
Example D
Spodoptera frugiperda test
5    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 with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-10    containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound=o— f the desired concentration and are populated with caterpillars of the armyworm (Spodopterafrugiperda), while the leaves are still moist.
15
After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed. The kill rates determined are calculated using Colby's formula (see page 39).
20    In this test, the following active compound combination in accordance with the present application
showed a synergistically enhanced activity compared to the active compounds applied on their own:
 
-47-
Table D: Plant-damaging insects
Spodoptera frugiperda test
Active compounds    Concentration of active
compound in ppm    Kill rate after
found*    in % 6d
calc.**
H3C
..-
H3C    0
N1    .../
CI    . H    CINI
    H3C 0    ;
CF3
(1-1-9)    0.032    75   
H3C
O    H3
NC
_    CI
-
114    CI
F
(2-3) betracyfluthrin    0.032    ----    0   
(I-1-9) + (2-3) betracyfluthrin (1:1)    0.032 + 0.032     100    75

* found    = activity found
** caic.    = activity calculated using Colby's formula
 
- 48 -
Claims
1.    A composition comprising a synergistically effective active compound combination of
anthranilamides of the formula (I)
R3\ R2
5         (I)

in ZN41 ich
AI and A2 independently of one another represent oxygen or sulfur,
XI    represents N or CR10,
R1    represents hydrogen or represents in each case optionally mono- or polysubstituted
10    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, C,-C4-alkoxy, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C4-alkoxycarbonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, (C,-C4-alkyl)C3-C6-cycloalkylamino
15    and RI I,
R2    represents hydrogen, CI-C6-alkyl, C2-C6-alkenyl, C2-C6-allcynyl, C3-C6-cycloalkyl,
C1-C4-alkoxy, C1-C4-alkylamino, C2-C8-dialkylanino, C3-C6-cycloalkylamino, C2-C6-alkoxycarkonyl or C2-C6-alkylcarbonyl,
represents hydrogen, R" or represents in each case optionally mono- or
20 polysubstituted C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C,-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C,-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl, R", phenyl, phenoxy and a 5- or 6-
25 membered heteroaromatic ring, where each phenyl, phenoxy and 5- or 6-membered 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,
 
-49-
R4    represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl,
C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio,
C1-C4-haloalkylsulfonyl, C2-C8-dialkylamino, C3-C6- cycloalkylamino, C3-C6-triallcylsilyl or represents in each case optionally mono- or polysubstituted phenyl, benzyl or phenoxy, where the substituents independently of one another may be selected from the group consisting of Cs-Cralkyl, C2-C4- alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C4-haloalkenyl,
10    C2-C4-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy,
C1-C4-haloalkoxy, C1-C4-alkylthio,    C1-C4-alkylsulfonyl, C1-C4-
allcylamino,    C2-C8-diallcylamino,    C3-C6-cycloalkylamino,    C3-C6-(alkyl)-
cycloalkylamino,    C2-C4-allcylcarbonyl,    C2-C6-alkoxycarbonyl,    C2-C6-alkyl-
aminocarbonyl, C3-C8-diallcylaminocarbonyl and C3-C6-trialkylsilyl,
15    11.5 and Rg in each case independently of one another represent hydrogen, halogen or
represent in each case optionally substituted C1-C4-alkyl, Cs-C4haloallcyl, R12, G, J, -OJ, -OG, -S(0)„-J, -S(0)p-G, -S(0) -phenyl, where the substituents independently of one another may be selected from one to three radicals W or from the group consisting of R12, C-Cso-alkyl, C2-C6-alkenyl, C2-C6-allcynyl, C1-C4-
 20        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, CI-C4- haloalkoxy, C1-C4-alkylthio, Cs-C4alkylsulfinyl, C1-C4-alkylsulfonyl,
haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino,
25  C2-C8-dia llcylamino, C3-C6-trialkylsilyl, 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,
in each case independently of one another represent a 5- or 6-membered
30  nonaromatic carbocyclic or heterocyclic ring which optionally contains one or two ring members from the group consisting of C(=0), 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,
35    C3-C7-cycloalkyl, (cyano)C3-C7-cycloalkyl, (C1-C4-alkyl)C3-C6-cycloalkyl, (C3-C6-
 
- 50 -
cycloalkyl)CI-Ca-alkyl, where each cycloalkyl, (alkyl)cycloalkyl and (cycloalkyl)¬alkyl may optionally be substituted by one or more halogen atoms,
.1    in each case independently of one another represent an optionally substituted 5- or
6-membered heteroaromatic ring, where the substituents independently of one
    5    another may be selected from one to three radicals W or one or more radicals RI',
R6    independently of one another represent -C(=E')R19, -LC(=EI)e, -C(=E')LRI9,
-LC(=EI)LR19, -0P(=Q)(0R19)2, -SO2LRI8 or -LSO2LR'9, where each E' independently of the others represents 0, S, N-R", N-OR", N-N(102, N-S=O, N-CN or N-NO2,
    10    R7    represents hydrogen, C,-C4-alkyl, C,-C4-haloalkyl, halogen, C,-C4-alkoxy, Ci-C4-
haloalkoxy, C,-C4-alkylthio, C,-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C,-C4-halo-
alkylthio, C,-C4-haloalkylsulfinyl, C,-C4-haloalkylsulfonyl,
R9;:-    represents C1-C4-haloalkyl, C,-C4-haloalkoxy, CI-Ca-baloallcylsulfinyl or halogen,
RI°    represents hydrogen, CI-Ca-alkyl, C,-C4-haloalkyl, halogen, cyano or CI-Ca-halo-
    15    alkoxy,
R"    in each case independently of one another represent in each case optionally mono-
to trisubstituted C,-C6-alkylthio, Ci-C6-alkylsulfenyl, CI-C6-haloallcythio, haloallcylsulfenyl, phenylthio or phenylsulfenyl, where the substituents independently of one another may be selected from the list consisting of W,
    20    -S(0)6N(R16)2,    -C(=0)12.13,    -L(C=0)R14,    -S(0=0)LR14,    -C(=0)LR13:
-S(0)nNR13q=0)R13, -S(0)„NR13C(=0)LR" and -S(0)6N1213S(0)2LR'4,
L    in each case independently of one another represent 0, NR's or S,
RI'    in each case independently of one another represent -B(OR'7)2, amino, SH, thio-
cyanato, C3-C8-trialkylsilyloxy, CI-Ca-alkyl disulfide, -SF5, -C(=E)12.19,
    25    -LC(=E)R'9, -C(=E)LR'9, -LC(=E)LR' 9,    -OP(=Q)(OR'9)2, -SO2LR'9 or
-LSO2LR19,
Q    represents 0 or S,
R'3    in each case independently of one another represent hydrogen or represent in each
case optionally mono- or poly substituted C,-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl
 30 or C3-C6-cyCloallcyl, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4¬alkoxy, C,-C4-alkylsulfinyl, CI-Ca-alkylsulfonyl, CI-Ca-alkylarnino, C2-Cg-dialkyl¬amino, C3-C6-cycloalkylamino and (CI-C4-alkyl)C3-C6-Cyclo'alkylamino,
R14    in each case independently of one another represent in each case mono- or
    35    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
 
-51-
group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4- allcylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6- cycloallcylamino and (C1-C4-alkyl)C3-C6-cycloalkylamino or represent optionally substituted phenyl, where the substituents independently of one another may be
    5    selected from one to three radicals W or one or more radicals R'2,
R15    in each case independently of one another represent hydrogen or represent in each
case mono- or polysubstituted CI-C6-haloallcyl or C1-C6-alkyl, where the
substituents independently of one another may be selected from the group
consisting of cyano, nitro, hydroxyl, CI-Cralkoxy, CI-C4haloalkoxy, C1-C4-
 10 alkylthio, C1-C4-allcylsulfonyl, C1-C4-haloalkylthio, C1-C4- haloalkylsulfinyl, C1-C4-haloallcylsulfonyl, C1-C4-allcylamino, C2-C8-diallcylamino, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl 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 R12, or N(R15)2
    15    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,
R'7    in each case independently of one another represent hydrogen or C1-C4-alkyl, or
B(OR17)2 represents a ring, where the two oxygen atoms are attached via a chain to
 20 two or 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,
R111    in each case independently of one another represent hydrogen, C1-C6-alkyl or
C1-C6-haloalkyl, or N(R13)(e) represents a cycle which forms the ring M,
 25 R19 in each case independently of one another represent hydrogen or represent in each case optionally 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-alkyl¬sulfinyl, C1-C4-alkylsulfonyl, Ci-Crhaloallcylthio, C1-C4-haloallcylsulfinyl, C1-C4-
 30 haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, CO2H, C2-C6-alkoxy-carbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W, C1-C6-haloalkyl, C3-C6-cycloallcyl or phenyl or pyridyl, each of which is optionally mono- to trisubstituted by W,
    35    M    in each case represents an optionally mono- to tetrasubstituted ring which, in
addition to the nitrogen atom which is attached to the substituent pair R13 and R",
 
- 52 -
 
(R15)2 or (R16)2, contains two to six carbon atoms and optionally additionally a further nitrogen, sulfur or oxygen atom, and where the substituents independently of one another may be selected from the group consisting of C1-C2-alkyl, halogen, cyano, nitro and C1-C2-alkoxy,
    5    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-halo-allcynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-allcylthio, C1-C4-alkylsulfinyl, C1-C4-allcylsulfonyl, C1-C4-alkyl-amino, C2-C8-dialkylamino, C3-C6-cycloallcylamino, (C1-C4-alkyl)C3-C6-
    10    cycloalkylamino, C2-C4-allcylcarbonyl, C2-C6-alkoxycarbonyl, CO2H, C2-C6-alkyl-
aminocarbonyl, C3-C8-dialkylaminocarbonyl or C3-C6-trialkylsilyl,
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,
    15    where in the case that (a) R5 represents hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-
haloalkenyl, C2-C6-haloalkynyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio or halogen and (b) R8 represents hydrogen, C1-C6-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
of R6, R11 and R12
    20    selected from the group consisting    is present and (d), if Rn is not present,
at least one R6 or R" is different from C2-C6-alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6- alkylaminocarbonyl and C3-C8-dialkylaminocarbonyl, and the compounds of the general formula (I) also include N-oxides and salts,
    25    and at least one active compound from the group of the pyrethroids (active compounds of
group 2) is synergistically effective and suitable for controlling animal pests.
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
IR2
 

 
in which
 
- 53 -
R2    represents hydrogen or C1-C6-alkyl,
R3    represents C1-C6-alkyl which is optionally substituted by a radical R6,
R4    represents C,-C4-alkyl,    C,-C2-haloalkoxy or halogen,
R5    represents hydrogen, C,-C4-alkyl, C,-C2-haloalkyl, CI-C2-haloalkoxy or halogen,
 5 R6 represents -C(=E2)RI9, -LC(=E2)R19, -C(=E2)L11.19 or -LC(=E2)LRI9, where each E2 independently of the others represents 0, S, N-R15, N-ORI5, N-N(RI5)2, and each L independently of the others represents 0 or NR",
R7    represents C,-C4-haloalkyl or halogen,
R9    represents C,-C2-haloalkyl, C,-C2-haloalkoxy, S(0)pCi-C2-haloallcyl or halogen,
 10 RI5 in each case independently of one another represent hydrogen or represent in each case optionally substituted C,-C6-haloalkyl or CI-C6-alkyl, where the substituent independently of one another may be selected from the group consisting of cyano, CI-Ca-alkoxy, C,-C4-haloalkoxy, C,-C4-alkylthio, CL=C4-allcylsulfinyl, C,-C4-alkyl-
_
sulfonyl, C,-C4-haloalkylthio, CI-Ca-haloallcylsulfinyl or CI-Ca-haloallcylsulfonyl,
    15    Rls    in each case represents hydrogen or C,-C4-alkyl,
RI9    in each case independently of one another represent hydrogen or CI-C6-alkyl,
p    independently of one another represents 0, 1, 2.
3.    The composition as claimed in claim 1 or 2 comprising at least one active compound from
    20    the group of the pyrethroids (active compounds of group 2) selected from
(2-1) acrinathrin
CF, 0
 
and/or
(2-3) betacyfluthrin
 
- 54 -
 
and/or
(2-4) cyhalothrin
CF,
CI
H3C     
    CH,    CN

5    and/or
cypermethrin
CI
 
and/or
(2-7) esfenvalerate
 
and/or
15    (2-8) ethofenprox
11,C20
and/or
 
and/or
10    (2-12) lambda-cyhalothrin
CH3 0
 

 
15    and/or
(2-14) taufluvalinate
F3C     

and/or
(2-15) tralomethrin
 
-56-
 
and/or
(2-16) zeta-cypermethrin
and/or
15    (2-20) eflusilanate,
 
and/or
(2-21) fubfenprox
 
-57-
 
 
 
 
 
5    R2° = -CH3 or -CO2CH3
R21= -CH=CH2 or -CH3 or -CH2CH3
and/or
(2-3) resmethrin
 

 
10    and/or
(2-24) gamma-cyhalothrin
H3C CH3
■•
F3C
OH CN
4.    The composition as claimed in claim 1, 2 or 3 comprising anthranilamides of the formula
15    (I) and at least one pyrethroid (group 2) in a ratio of from 50:1 to 1:5.
5.    The use of a synergistically effective mixture comprising compounds of the formula (I) as set forth in claim 1 or 2 and at least one pyrethroid (group 2) for controlling animal pests.
20    6.    A process for preparing pesticides, characterized in that a synergistically effective mixture
comprising compounds of the formula (I) as set forth in claim I or 2 and at least One pyrethroid (group 2) are mixed with extenders and/or surfactants.
 
-5s -
II fad. 'tu    with imeAcidW Ifl KrLics
A b.strac.i.
The imvaliou !Oaks io 11•0Vel ineeatitidal Ncliva compour_d ceertiiirulikPas coatisting firmly,. of antbranilamidei aid, sty:wily, of furthr imodicidarly ac -v eoriperuhis Irvin the grow of lc pyrrthroick. Which combinations ace bighty 2uitible fay coccrelloix ink"' peut
 
indeetion.Ist QCOK tags.Ist

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