CN100393208C - Active substance combination having insecticidal and acaricide properties - Google Patents

Active substance combination having insecticidal and acaricide properties Download PDF

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CN100393208C
CN100393208C CNB2004800361767A CN200480036176A CN100393208C CN 100393208 C CN100393208 C CN 100393208C CN B2004800361767 A CNB2004800361767 A CN B2004800361767A CN 200480036176 A CN200480036176 A CN 200480036176A CN 100393208 C CN100393208 C CN 100393208C
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CN1889835A (en
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克里斯蒂安·冯克
赖讷·菲舍尔
吕迪格尔·菲舍尔
H·亨格伯格
W·安德施
沃尔夫甘·蒂莱尔特
A·克劳斯
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Bayer Intellectual Property GmbH
Bayer CropScience AG
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

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Abstract

The invention relates to novel active substance combinations comprising cyclic keto-enols or other insecticides and additional insecticides from the group of anthranilic acid amines. Said active substance combinations are very suitable for controlling animal pests such as insects and undesired mites.

Description

Active ingredient combinations having insecticidal and acaricidal properties
The present invention relates to novel active compound combinations comprising: firstly, known cyclic ketoenols (cyclic ketoenols) and, secondly, known insecticidally active compounds, which combinations are particularly suitable for controlling animal pests, such as insects and unwanted acarids.
Certain cyclic ketoenols are known to have herbicidal, insecticidal and acaricidal properties. The activity of these compounds is good, but not always satisfactory at low application rates.
Unsubstituted bicyclic 3-arylpyrrolidine-2, 4-dione derivatives (EP-A0355599 and EP-A0415211) and substituted monocyclic 3-arylpyrrolidine-2, 4-dione derivatives (EP-A0377893 and EP-A0442077) which have herbicidal, insecticidal or acaricidal action are known.
Polycyclic 3-arylpyrrolidine-2, 4-dione derivatives (EP-A0442073) and 1H-arylpyrrolidine-dione derivatives (EP-A0456063, EP-A0521334, EP-A0596298, EP-A0613884, EP-A0613885, WO 94/01997, WO 95/26954, WO 95/20572, EP-A0668267, WO 96/25395, WO 96/35664, WO 97/01535, WO 97/02243, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO 99/43649, WO 99/48869 and WO 99/55673, WO 01/23354, WO 01/74770) are also known. The activity of these compounds is good, but is not always satisfactory at low application rates.
Mixtures of phthalamides and other biologically active compounds are also known to have insecticidal and/or acaricidal action (WO 02/087334). However, the activity of such mixtures is not always optimal.
Furthermore, various heterocyclic compounds, organotin compounds, benzoylureas and pyrethroids are known to have insecticidal, acaricidal properties (cf. WO 93/22297, WO 93/10083, DE-A2641343, EP-A0347488, EP-A0210487, US 3,364,177 and EP-A234045). However, the activity of these compounds is likewise not always satisfactory.
It has now been found that mixtures of compounds of group 1 of the formula (I) or active compounds of group 2 having insecticidal activity with at least one active compound from the anthranilamide group of the formula (II) have a synergistic effect and have particularly good insecticidal and acaricidal activity,
the compound of formula (I) in group 1 is
Figure C20048003617600041
Wherein
X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
W1y and Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
A3represents hydrogen, alkyl, alkoxyalkyl, in each case optionally substituted by halogen, optionally substituted saturated cycloalkyl, optionally at least one ring member being replaced by a heteroatom,
A4represents hydrogen or an alkyl group,
A3and A4Together with the carbon atom to which they are attached represent a saturated or unsaturated, substituted or unsubstituted ring, said ring optionally containing at least one heteroatom,
d represents hydrogen, or optionally substituted alkyl, alkenyl, alkoxyalkyl, saturated cycloalkyl, optionally one or more ring members being replaced by heteroatoms,
A3and D together with the atoms to which it is attached represents a saturated or unsaturated ring, said ring being described at A3The moiety D is unsubstituted or substituted and optionally contains at least one heteroatom,
G1represents hydrogen (a) or represents one of the following groups
Figure C20048003617600042
E represents a metal ion or an ammonium ion,
L1represents oxygen or sulfur, and is selected from the group consisting of,
M1represents oxygen or sulfur, and is selected from the group consisting of,
R20represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, each of which is optionally substituted by halogen; or cycloalkyl optionally substituted by halogen, alkyl or alkoxy, which may be interrupted by at least one heteroatom; phenyl, phenylalkyl, heteroaryl, phenoxyalkyl or heteroaryloxyalkyl, each of which is optionally substituted,
R21represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, each of which is optionally substituted by halogen, or represents cycloalkyl, phenyl or benzyl, each of which is optionally substituted,
R22represents an optionally halogen-substituted alkyl group, or an optionally substituted phenyl group,
R23and R24Independently of one another, represents alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio, each of which is optionally substituted by halogen, or represents phenyl, benzyl, phenoxy or phenylthio, each of which is optionally substituted, and
R25and R26Independently of one another, represents hydrogen, alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each of which is optionally substituted by halogen, represents optionally substituted phenyl, represents optionally substituted benzyl, or together with the nitrogen atom to which it is attached represents an optionally substituted ring, which is optionally interrupted by oxygen or sulfur,
the active compounds of group 2 having insecticidal activity are preferably
(2-1) Chlorfenamidine (amitraz) (known from DE-A2061132)
And/or
(2-2) Buprofezin (known from DE-A2824126)
Figure C20048003617600052
And/or
(2-3) triazamate (known from EP-A0213718)
Figure C20048003617600053
And/or
(2-4) pymetrozine (known from EP-A0314615)
Figure C20048003617600054
And/or
(2-5) pyriproxyfen (known from EP-A0128648)
Figure C20048003617600061
And/or
(2-6) flonicamid (flonicamid) (known from EP-A0580374)
Figure C20048003617600062
And/or
(2-7) resistance to aphids (pirimicarb) (known from GB 1181657)
Surprisingly, the insecticidal and/or acaricidal activity of the active compound combinations according to the invention is higher than the sum of the activities of the individual active compounds. Thus, there is an unforeseeable real synergistic effect, rather than a simple addition of activities.
In addition to at least one active compound of the formula (I) or one active compound of group 2 (compounds (2-1) to (2-7)), the active compound combinations according to the invention also contain at least one active compound of the formula (II).
Preference is given to active compound combinations comprising a compound of the formula (I) in which,
W1represents hydrogen, C1-C4Alkyl radical, C1-C4Alkoxy, chlorine, bromine or fluorine,
x represents C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Haloalkyl, fluorine, chlorine or bromine,
y and Z independently of one another represent hydrogen, C1-C4Alkyl, halogen, C1-C4Alkoxy or C1-C4A halogenated alkyl group,
A3represents hydrogen or C, each of which is optionally substituted by halogen1-C6Alkyl or C3-C8A cycloalkyl group,
A4represents hydrogenA methyl group or an ethyl group, or a salt thereof,
A3and A4And also together with the carbon atom to which they are attached represent saturated C3-C6Cycloalkyl in which optionally one ring atom is replaced by oxygen or sulphur and which is optionally substituted by C1-C4Alkyl, trifluoromethyl or C1-C4The alkoxy group is mono-or di-substituted,
d represents hydrogen, C each optionally substituted by fluorine or chlorine1-C6Alkyl radical, C3-C4Alkenyl or C3-C6A cycloalkyl group,
A3and D together represent C optionally substituted by methyl3-C4Alkanediyl, wherein optionally one methylene group is replaced by thio,
G1represents hydrogen (a) or represents one of the following groups
E (f) or
Figure C20048003617600072
(g) In particular (a), (b), (c) or (g)
E represents a metal ion or an ammonium ion,
L1represents oxygen or sulfur, and is selected from the group consisting of,
M1represents oxygen or sulfur, and is selected from the group consisting of,
R20represents C, each of which is optionally substituted by halogen1-C10Alkyl radical, C2-C10Alkenyl radical, C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, or optionally fluoro, chloro, C1-C4Alkyl or C1-C2Alkoxy-substituted C3-C6A cycloalkyl group,
represents optionally fluorine, chlorine, bromine, cyano, nitro, C1-C4Alkyl radical, C1-C4Alkoxy-, trifluoromethyl-or trifluoromethoxy-substituted phenyl,
represents pyridyl or thienyl, each of which is optionally substituted by chlorine or methyl,
R21represents C, each of which is optionally substituted by fluorine or chlorine1-C10Alkyl radical, C2-C10Alkenyl radical, C1-C4Alkoxy radical C2-C4An alkyl group, a carboxyl group,
represents C optionally substituted by methyl or methoxy5-C6Cycloalkyl radicals, or
Represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4Alkyl radical, C1-C4Alkoxy-, trifluoromethyl-or trifluoromethoxy-substituted phenyl or benzyl,
R22represents C optionally substituted by fluorine1-C4Alkyl or represents optionally fluorine, chlorine, bromine, C1-C4Alkyl radical, C1-C4Alkoxy-, trifluoromethyl-, trifluoromethoxy-, cyano-or nitro-substituted phenyl,
R23represents C, each of which is optionally substituted by fluorine or chlorine1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Alkylamino radical, C1-C4Alkylthio, or represents in each case optionally fluorine, chlorine, bromine, nitro, cyano, C1-C4Alkoxy, trifluoromethoxy, C1-C4Alkylthio radical, C1-C4Haloalkylthio, C1-C4Alkyl-or trifluoromethyl-substituted phenyl, phenoxy or phenylthio,
R24represents C1-C4Alkoxy orC1-C4An alkylthio group is a group of one or more,
R25represents C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy radical, C3-C6Alkenyl radical, C1-C4Alkoxy radical C1-C4An alkyl group, a carboxyl group,
R26represents C1-C6Alkyl radical, C3-C6Alkenyl or C1-C4Alkoxy radical C1-C4An alkyl group, a carboxyl group,
R25and R26Together also represent C optionally substituted by methyl or ethyl3-C6Alkenyl, wherein optionally one carbon atom is replaced by oxygen or sulphur.
Within the preferred scope of the halogen radicals, halogen preferably represents chlorine and fluorine.
Particular preference is given to active compound combinations comprising a compound of the formula (I) in which the compound is present and at least one active compound of the formula (II)
W1Represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy,
x represents chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy or trifluoromethyl,
y and Z independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or methoxy,
A3represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
A4represents hydrogen, a methyl group or an ethyl group,
A3and A4And also together with the carbon atom to which they are attached represent saturated C6Cycloalkyl, optionally one ring member being oxoAnd optionally mono-substituted by methyl, ethyl, methoxy, ethoxy, propoxy or butoxy,
d represents hydrogen, represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, allyl, cyclopropyl, cyclopentyl or cyclohexyl,
A3and D together represent C optionally substituted by methyl3-C4An alkanediyl group, which is a cyclic alkyl group,
G1represents hydrogen (a) or represents one of the following groups,
Figure C20048003617600081
or
Figure C20048003617600082
L1Represents oxygen or sulfur, and is selected from the group consisting of,
M1represents oxygen or sulfur, and is selected from the group consisting of,
R20represents C1-C8Alkyl radical, C2-C4Alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl,
represents phenyl which is optionally mono-to disubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,
represents pyridyl or thienyl, each of which is optionally mono-to disubstituted by chlorine or methyl,
R21represents C1-C8Alkyl radical, C2-C4Alkenyl, methoxyethyl, ethoxyethyl, or represents phenyl or benzyl,
R25and R26Independently of one another, methyl, ethyl or, together with the nitrogen atom to which they are attached, morpholineAnd (4) generation.
Particular preference is given to active compound combinations comprising a compound of the formula (I) in which the compound is present and at least one active compound of the formula (II)
W1Represents hydrogen or a methyl group,
x represents chlorine, bromine or methyl,
y and Z independently of one another represent hydrogen, chlorine, bromine or methyl,
A3and A4And also together with the carbon atom to which they are attached represent saturated C6Cycloalkyl, optionally one ring member being replaced by oxygen and optionally mono-substituted by methyl, methoxy, ethoxy, propoxy or butoxy,
d represents hydrogen, and the compound (D) represents hydrogen,
G1represents hydrogen (a) or represents one of the following groups
Figure C20048003617600091
Or
Figure C20048003617600092
L1Represents oxygen or sulfur, and is selected from the group consisting of,
M1represents oxygen or sulfur, and is selected from the group consisting of,
R20represents C1-C8Alkyl radical, C2-C4Alkenyl, methoxymethyl, ethoxymethyl, ethylmethylthio, cyclopropyl, cyclopentyl, cyclohexyl,
represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
represents pyridyl or thienyl, each of which is optionally mono-substituted by chlorine or methyl,
R21represents C1-C8Alkyl radical, C2-C4Alkenyl, methoxyethyl, ethoxyethyl, phenyl or benzyl,
R25and R26Independently of one another, represents methyl, ethyl or, together with the nitrogen atom to which they are attached, represents morpholino.
Active compound combinations comprising at least one compound of the formula (I-a) below and at least one active compound of the formula (II) are very particularly preferred.
Figure C20048003617600101
Very particularly preferably active compound combinations comprising a compound of the formula (I-a-4) and at least one active compound of the formula (II)
Figure C20048003617600103
Among the various properties, the compounds of the formula (I) may, depending primarily on the nature of the substituents, be present as geometric and/or optical isomers or as mixtures of isomers of different composition, which mixtures may, if appropriate, be separated in a customary manner. The present invention provides pure isomers and isomer mixtures, processes for their preparation and their use, and compositions containing them. However, for the sake of simplicity, it will be referred to hereinafter only as a compound of formula (I), but this term is intended to mean both the pure compound and, where appropriate, a mixture of isomeric compounds in different proportions.
Active compound combinations comprising compounds from group 2 (2-1) to (2-7) and at least one active compound of the formula (II) are very particularly preferred.
Anthranilamides of the formula (II) are likewise known compounds, which are described in or include the corresponding publications:
WO 01/70671、WO 03/015518、WO 03/015519、WO 03/016284、WO03/016282、WO 03/016283、WO 03/024222、WO 03/062226。
the general formulae and definitions mentioned in the above publications and the individual compounds mentioned therein are expressly incorporated in this description by reference.
Anthranilamides can be represented by the following formula (II):
wherein,
A1and A2Independently of one another represent oxygen or sulphur,
X1represents N or CR10，
R1Represents hydrogen or represents C, each of which is optionally substituted by one or more1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl or C3-C6Cycloalkyl, wherein the substituents independently of each other may be selected from R6Halogen, cyano, nitro, hydroxy, C1-C4Alkoxy radical, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C2-C4Alkoxycarbonyl group, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C3-C6Cycloalkylamino group, (C)1-C4Alkyl) C3-C6Cycloalkylamino and R11，
R2Represents hydrogen, C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C3-C6Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C3-C6Cycloalkylamino, C2-C6Alkoxycarbonyl or C2-C6An alkyl-carbonyl group, a carboxyl group,
R3represents hydrogen, R11Or represents C which is in each case optionally mono-or polysubstituted1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C3-C6Cycloalkyl, wherein the substituents independently of each other may be selected from R6Halogen, cyano, nitro, hydroxy, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C2-C6Alkoxycarbonyl group, C2-C6Alkylcarbonyl group, C3-C6Trialkylsilyl group R11Phenyl, phenoxy and a 5-or 6-membered heteroaromatic ring, wherein the phenyl, phenoxy and 5-or 6-membered heteroaromatic ring may each optionally be substituted, which substituents independently of one another may be selected from one to three W groups or one or more R12The radical, or,
R2and R3May be connected to each other to form a ring M,
R4represents hydrogen, C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C3-C6Cycloalkyl radical, C1-C6Haloalkyl, C2-C6Haloalkenyl, C2-C6Halogenated alkynyl, C3-C6Halocycloalkyl, halogen, cyano, nitro, hydroxy, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Haloalkylthio, C1-C4Haloalkylsulfinyl radical, C1-C4Haloalkylsulfonyl group, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C3-C6Cycloalkylamino, C3-C6Trialkylsilyl or represents in each case optionally mono-or polysubstituted phenyl, benzyl or phenoxy, where the substituents may, independently of one another, be chosen from C1-C4Alkyl radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C3-C6Cycloalkyl radical, C1-C4Haloalkyl, C2-C4Haloalkenyl, C2-C4Halogenated alkynyl, C3-C6Halocycloalkyl, halogen, cyano, nitro, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C3-C6Cycloalkylamino, C3-C6(alkyl) cycloalkylamino, C2-C4Alkylcarbonyl group, C2-C4Alkoxycarbonyl group, C2-C6Alkylaminocarbonyl radical, C3-C8Dialkylaminocarbonyl and C3-C6A trialkyl silyl group,
R5and R8Each independently of the others, represents hydrogen, halogen or represents in each case optionally substituted C1-C4Alkyl radical, C1-C4Haloalkyl, R12、G、J、-OJ、-OG、-S(O)p-J、-S(O)p-G、-S(O)p-benzeneWherein the substituents independently of one another may be selected from one to three W groups or from R12、C1-C10Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C4Alkoxy and C1-C4Alkylthio, wherein the substituents may each be independently selected from G, J, R6Halogen, cyano, nitro, amino, hydroxy, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Haloalkylthio, C1-C4Haloalkylsulfinyl radical, C1-C4Haloalkylsulfonyl group, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C3-C6Trialkylsilyl, phenyl and phenoxy substituents, wherein each phenyl ring or phenoxy ring may optionally be substituted, which substituents independently of one another may be selected from one to three W groups or one or more R12The radical(s) is (are),
each G independently of the others represents a 5-or 6-membered non-aromatic carbocyclic or heterocyclic ring optionally containing one or two members selected from C (═ O), SO and S (═ O)2And said rings may optionally be substituted by one to four substituents independently of each other selected from C1-C2Alkyl, halogen, cyano, nitro and C1-C2Substituent substitution of alkoxy; or independently of one another represent C2-C6Alkenyl radical, C2-C6Alkynyl, C3-C7Cycloalkyl, (cyano) C3-C7Cycloalkyl group, (C)1-C4Alkyl) C3-C6Cycloalkyl group, (C)3-C6Cycloalkyl) C1-C4Alkyl, wherein each of cycloalkyl, (alkyl) cycloalkyl and (cycloalkyl) alkyl may be optionally substituted by one or more halogen atoms,
j each independently of the others represents an optionally substituted 5-or 6-membered heteroaromatic radicalRing, wherein the substituents independently of each other may be selected from one to three W groups or one or more R12The radical(s) is (are),
R6independently of one another, represents-C (═ E)1)R19、-LC(＝E1)R19、-C(＝E1)LR19、-LC(＝E1)LR19、-OP(＝Q)(OR19)2、-SO2LR18or-LSO2LR19Wherein each E1Represent, independently of one another, O, S, N-R15、N-OR15、N-N(R15)2N-S-O, N-CN or N-NO2，
R7Represents hydrogen, C1-C4Alkyl radical, C1-C4Haloalkyl, halogen, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Haloalkylthio, C1-C4Haloalkylsulfinyl radical, C1-C4A halogenated alkylsulfonyl group,
R9represents C1-C4Haloalkyl, C1-C4Haloalkoxy, C1-C4A haloalkylsulfinyl group or a halogen,
R10represents hydrogen, C1-C4Alkyl radical, C1-C4Haloalkyl, halogen, cyano, or C1-C4A halogenated alkoxy group,
R11each independently of the others represents C which is in each case optionally mono-to trisubstituted1-C6Alkylthio radical, C1-C6Alkylsulfinyl (sulfinyl), C1-C6Haloalkylthio, C1-C6Haloalkylsulfinyl, thiophenyl or phenylsulfinyl, wherein the substituents independently of one another can be selected from W, -S (O)nN(R16)2、-C(＝O)R13、-L(C＝O)R14、-S(C＝O)LR14、-C(＝O)LR13、-S(O)nNR13C(＝O)R13、-S(O)nNR13C(＝O)LR14or-S (O)nNR13S(O)2LR14，
L each independently of the others represents O, NR18Or the number of the S-beams is,
R12each independently of the other represents-B (OR)17)2Amino, SH, thiocyanato, C3-C8Trialkylsiloxy, di (C)1-C4Alkyl) dithio (C)1-C4-alkyldisulfide)、-SF5、-C(＝E1)R19、-LC(＝E1)R19、-C(＝E1)LR19、-LC(＝E1)LR19、-OP(＝Q)(OR19)2、-SO2LR19or-LSO2LR19，
Q represents O or S, and Q represents O or S,
R13each independently of the other represents hydrogen or represents C, each optionally substituted by one or more1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl or C3-C6Cycloalkyl, wherein the substituents independently of each other may be selected from R6Halogen, cyano, nitro, hydroxy, C1-C4Alkoxy radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C3-C6Cycloalkylamino or (C)1-C4Alkyl) C3-C6A cycloalkylamino group,
R14each independently of the others represents C, each optionally substituted by one or more1-C20Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl or C3-C6Cycloalkyl, wherein the substituents independently of each other may be selected from R6Halogen, cyano, nitro, hydroxy, C1-C4Alkoxy radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C3-C6Cycloalkylamino and (C)1-C4Alkyl) C3-C6Cycloalkylamino, or represents optionally substituted phenyl, the substituents of which independently of one another may be selected from one to three W groups or one or more R12The radical(s) is (are),
R15each independently of the other represents hydrogen or represents C, each optionally substituted by one or more1-C6Haloalkyl or C1-C6Alkyl, wherein the substituents independently of one another may be selected from cyano, nitro, hydroxy, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Haloalkylthio, C1-C4Haloalkylsulfinyl radical, C1-C4Haloalkylsulfonyl group, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C2-C6Alkoxycarbonyl group, C2-C6Alkylcarbonyl group, C3-C6Trialkylsilyl, and optionally substituted phenyl, the substituents of which independently of one another may be selected from one to three W groups or one or more R12A group; or N (15)2Represents a ring forming the ring M,
R16represents C1-C12Alkyl or C1-C12Haloalkyl, or N (R)16)2Represents a ring forming the ring M,
R17each independently of the others represents hydrogen or C1-C4Alkyl, OR B (OR)17)2Represents a ring in which two oxygen atoms are connected by a chain having two to three carbon atoms optionally substituted by one or two groups independently of each other selected from methyl and C2-C6The substituent group of the alkoxy carbonyl group is substituted,
R18each independently of the others represents hydrogen, C1-C6Alkyl or C1-C6Haloalkyl, or N (R)13)(R18) Represents a ring forming the ring M,
R19each independently of the other represents hydrogen or represents C, each optionally substituted by one or more1-C6Alkyl, wherein the substituents independently of one another may be selected from cyano, nitro, hydroxy, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Haloalkylthio, C1-C4Haloalkylsulfinyl radical, C1-C4Haloalkylsulfonyl group, C1-C4Alkylamino radical, C2-C8Dialkylamino, CO2H、C2-C6Alkoxycarbonyl group, C2-C6Alkylcarbonyl group, C3-C6Trialkylsilyl and optionally substituted phenyl, wherein the substituents independently of one another can be selected from one to three W groups, C1-C6Haloalkyl, C3-C6Cycloalkyl or phenyl or pyridyl each optionally mono-to trisubstituted by W,
each M represents an optionally mono-to tetrasubstituted ring, said ring except containing a substituent pair R13And R18、(R15)2Or (R)16)2Containing, in addition to the nitrogen atom to which it is attached, two to six carbon atoms and optionally one further nitrogen, sulfur or oxygen atom, wherein the substituents independently of one another may be selected from C1-C2Alkyl, halogen, cyano, nitro and C1-C2An alkoxy group,
each W independently of the other represents C1-C4Alkyl radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C3-C6Cycloalkyl radical, C1-C4Haloalkyl, C2-C4Haloalkenyl, C2-C4Halogenated alkynyl, C3-C6Halocycloalkyl, halogen, cyano, nitro, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Alkylamino radical, C2-C8Dialkylamino radical, C3-C6Cycloalkylamino group, (C)1-C4Alkyl) C3-C6Cycloalkylamino, C2-C4Alkylcarbonyl group, C2-C6Alkoxycarbonyl, CO2H、C2-C6Alkylaminocarbonyl radical, C3-C8Dialkylaminocarbonyl or C3-C6A trialkyl silyl group,
each n independently of the others represents 0 or 1,
each p, independently of the others, represents 0, 1 or 2,
wherein, in (a) R5Represents hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C2-C6Haloalkenyl, C2-C6Halogenated alkynyl, C1-C4Haloalkoxy, C1-C4Haloalkylthio or halogen, and (b) R8Represents hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C2-C6Haloalkenyl, C2-C6Halogenated alkynyl, C1-C4Haloalkoxy, C1-C4Haloalkylthio, halogen, C2-C4Alkylcarbonyl group, C2-C6Alkoxycarbonyl group, C2-C6Alkylaminocarbonyl or C3-C8In the case of a dialkylaminocarbonyl group, (c) at least one R selected from R is present6、R11And R12And (d) if R is absent12Then at least one R6Or R11Is different from C2-C6Alkylcarbonyl group, C2-C6Alkoxycarbonyl group, C2-C6Alkylaminocarbonyl or C3-C8A dialkylaminocarbonyl group.
The compounds of the general formula (II) also include N-oxides and salts.
Among the various properties, the compounds of formula (II) may, depending mainly on the nature of the substituents, be present as geometric and/or optical isomers or as mixtures of isomers of different composition, which mixtures may be separated, if desired, in a conventional manner. The present invention provides pure isomers and isomer mixtures, processes for their preparation and their use, and compositions containing them. However, for the sake of simplicity, it will be referred to hereinafter only as the compound of formula (II), but this term is intended to mean both the pure compound and, if appropriate, also a mixture of isomeric compounds in different proportions.
Preference is given to active compound combinations comprising compounds of the formula (II-1),
Figure C20048003617600161
wherein,
R2represents hydrogen or C1-C6An alkyl group, a carboxyl group,
R3represents optionally substituted by one R6Substituted C1-C6An alkyl group, a carboxyl group,
R4represents C1-C4Alkyl radical, C1-C2HalogenatedAlkyl radical, C1-C2A haloalkoxy group or a halogen, or a pharmaceutically acceptable salt thereof,
R5represents hydrogen, C1-C4Alkyl radical, C1-C2Haloalkyl, C1-C2A haloalkoxy group or a halogen, or a pharmaceutically acceptable salt thereof,
R6represents-C (═ E)2)R19、-LC(＝E2)R19、-C(＝E2)LR19or-LC (═ E)2)LR19Wherein each E2Represent, independently of one another, O, S, N-R15、N-OR15、N-N(R15)2And each L independently of one another represents O or NR18，
R7Represents C1-C4A haloalkyl group or a halogen,
R9represents C1-C2Haloalkyl, C1-C2Haloalkoxy, S (O)pC1-C2A haloalkyl group or a halogen,
R15each independently of the other represents hydrogen or represents in each case optionally substituted C1-C6Haloalkyl or C1-C6Alkyl, wherein the substituents independently of one another may be selected from cyano, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Haloalkylthio, C1-C4Haloalkylsulfinyl or C1-C4A halogenated alkylsulfonyl group,
R18each represents hydrogen or C1-C4An alkyl group, a carboxyl group,
R19each independently of the others represents hydrogen or C1-C6An alkyl group, a carboxyl group,
p represents independently of one another 0, 1, 2.
In the radical definitions mentioned as preferred, halogen stands for fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
Particular preference is given to active compound combinations comprising compounds of the formula (II-1) in which,
R2represents hydrogen or a methyl group,
R3represents C1-C4Alkyl (in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl),
R4represents methyl, trifluoromethyl, trifluoromethoxy, fluorine, chlorine, bromine or iodine,
R5represents hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl or trifluoromethoxy,
R7represents chlorine or bromine, and is selected from the group consisting of,
R9represents trifluoromethyl, chlorine, bromine, difluoromethoxy or trifluoroethoxy.
Active compound combinations comprising a compound of the following formula (II-1) and an active compound of group 1 of formula (I) or a compound of group 2 selected from the compounds (2-1) to (2-7) are particularly preferred:
Figure C20048003617600181
Figure C20048003617600182
Figure C20048003617600191
very particular preference is given to active compound combinations comprising a compound of the formula and an active compound of group 1 of the formula (I) or a compound of group 2 selected from the compounds (2-1) to (2-7).
Figure C20048003617600201
Figure C20048003617600211
Figure C20048003617600221
Figure C20048003617600231
Figure C20048003617600241
The following active compound combinations comprising compounds of the formula (II-1-9) and the active compounds of the above-mentioned group 1 of the formula (I) or of the active compounds of group 2 are emphasized:
a) active compound combinations comprising (II-1-9) and (I-a-4).
b) Active compound combinations containing (II-1-9) and (2-2) buprofezin.
c) Active compound combinations containing (II-1-9) and (2-6) flonicamid.
d) Active compound combinations containing (II-1-9) and (2-7) pirimicarb.
The following active compound combinations (binary mixtures) containing a compound of the formula (I) or a compound of group 2, and a compound of the formula (II-1) are emphasized:
Figure C20048003617600242
Figure C20048003617600251
Figure C20048003617600261
Figure C20048003617600281
however, the broad or preferred radical definitions or explanations mentioned above can also be combined with one another as desired, i.e. between the respective ranges and preferred ranges. The definitions apply to the final products and correspondingly to the precursors and intermediates.
Preferred active compound combinations according to the invention contain a compound of the formula (I) or a compound of group 2 and at least one compound of the formula (II), where the radicals are combinations of the above-mentioned preferred (preferred) definitions.
Particularly preferred active compound combinations according to the invention contain a compound of the formula (I) or a compound of group 2 and at least one compound of the formula (II), where the radicals are combinations as defined above with particular preference.
Particularly preferred active compound combinations according to the invention contain a compound of the formula (I) or a compound of group 2 and at least one compound of the formula (II), where the radicals are the combinations defined above as being particularly preferred.
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, and even those bound to heteroatoms, such as alkoxy, can each be linear or branched, respectively.
The optionally substituted radicals may be mono-or polysubstituted, where in the case of polysubstitution the substituents may be identical or different.
Furthermore, the active compound combinations may also contain other fungicidal, acaricidal or insecticidal co-ingredients (co-ingredients).
The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in a certain weight ratio. The desired ratio to achieve a synergistic effect need not be the preferred mixing ratio to achieve 100% activity. As such, the weight ratio of active compound in the active compound combination may vary within a rather wide range. In general, the combinations according to the invention contain the active compounds of the formula (I) or the group 2 compounds and the second group mixture components in the following preferred and particularly preferred mixing ratios:
the mixing ratio is weight ratio. The ratio is understood to mean the active compounds of the formula (I): mixed component (mixing partner)
Figure C20048003617600291
The active compound combinations according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are present in agriculture, in animal health, in forestry, in horticulture and in leisure facilities, in the protection of stored goods and materials and in sanitary environments, and at the same time exhibit good plant tolerance, low toxicity to warm-blooded animals and good environmental compatibility. They are active against normally sensitive and resistant species, and all or a single developmental stage. The pests include:
isopoda (Isopoda), for example, white-eared beetle (Oniscus asellus), Armadillium vulgare (Armadillidium vulgare), Armadillidium globosum (Porcellio scaber).
From the order of the Diplopoda (Diplopoda), for example, Blaniulus guttulatus.
From the order of the Chilopoda (Chilopoda), for example, Geophilus carpophagus, Scutigerispp.
For general purposes (Symphyla), for example, Scutigerella immacula.
From the order of the Thysanura, for example, Chlamydomonas (Lepisma saccharana).
From the order of the Collelmola (Collelmbola), for example, Onychiurus armatus (Onychiurus armatus).
From the order of the Orthoptera (Orthoptera), for example, cricket-tree (Acheta domestica), Gryllotalpa spp, African migratory locusts (Lousta migratoriatoides), Black locust (Melanoplus spp), desert locust (Schistocerca gregaria).
From the order of the Blattaria (Blattaria), for example, Blatta orientalis (Blatta orientalis), Periplaneta americana (Periplaneta americana), Bladella maderae (Leucophaea germanae), Blatta germanica (Blattaria germanica).
From the Dermaptera (Dermaptera), for example, Forficula auricularia (Forficula auricularia).
From the order of the Isoptera (Isoptera), for example, the Reticulitermes spp.
From the order of the Phtiaphthirales (Phthiraptera), for example, Pediculus humanus (Pediculus humanus murroris), Pediculus humanus species (Haematopinus spp.), Pediculus humanus species (Linogaphus spp.), Pediculus humanus species (Trichoderma spp.), and Pediculus anidae species (Damalinia spp.).
From the order of the Thysanoptera (Thysanoptera), for example, Thrips palmi (Hercinothrips femoralis), Thrips tabaci (Thrips tabaci), Thrips palmi (Thrips palmi), Thrips lucernifolia (Frankliniella accidentalis).
From the order of the Heteroptera (Heteroptera), for example, the species Douglas bugs (Eurygaster spp.), Dysdercus intermedius, Blastus squaratus (Piesma quadrata), Cimex lectularius (Cimex lectularius), Nepholus longirostratus (Rhodnius prolixus), Nepholygus droguensis (Triatoma spp.).
Homoptera, for example, whitefly brassicae (Aleurodeses brassicae), whitefly cassava (Bemis tabaci), whitefly greenhouse (Trialeurodes vaporariorum), Aphis gossypii (Aphis gossypii), Aphis brassicae (Brevicornus brassicae), Cryptophycus theophylli (Cryptomyces terreus), Aphis saccharina (Aphis fabae), Aphis applanatus (Aphis sphaeroides), Aphis woolli (Eriosoma lanigerum), Aphis metschlegelii (Hyalophorus lucidus), Portugineus vitis (Phyllopteroma grandis), Portugineus vitis (Phyllopterura staphylx), Aphis gophycus (Pemphigus spp.), Aphis gramineus (Phyllophora glauca), Aphis virginosa (Phyllophora glauca), Phyllophora virginosa (Phyllophora), Phyllophora viridans (Phyllophora), Phyllophora viridis, Phyllophora viridula (Phyllophora), Phyllophora spp), Phyllophora viridula (Phyllophora), Phyllophora spp.), Eupatula (Phyllophora spp.), Eupatula spp.), Nepholus spp (Phyllophora spp.), Neurospora spp (Neurospora spp.), Neurospora spp (Neurospora spp. (Neuro, Pediculosis species (Psylla spp.).
Lepidoptera (Lepidoptera), for example, Henry diamondback moth (Pectinophoragossypiella), looper (Bupalus piniarius), winter-size moth (Cheimatobirudia), Plumbum xylostella (Lithocolletis blancardella), apple moth (Hypomeuta padela), Plutella xylostella (Plutella xylostella), yellow-brown cutworm (Malacosa neustria), yellow-moth (Euproctis chrysospora), Pothida species (Lyotricha spp.), cotton latent moth (Buccnaturaria thunbergii), Phylophilus citrus latent species (Phyllostis citrus ostreatus), Geotrichum species (Agrostis spp.), Chelidota Sporida species (Sporidia spp.), Sporidia sp., Sp, Mediterranean meal moth (Ephemeria kuehniella), pyralidae medinalis (Galleria mellonella), Trichoplusia bissella, Bombycis mori (Tenebia pellionella), Bombycis mori (Tenebia pellioniana), Brown moths (Hofmenophila pseudostella), Linearia virescens (Cacoecia podana), Capua retena, Colostrinia furnacalis (Choristoneura furifera), grape fruit moth (Clysia ambiguella), tea leaf roller moth (Homona Cnmagnanima), oak green roller moth (Torx virginana), aphalocerus rupestris pp., Rice negative mud worm (Oulemaryzae).
Coleoptera, e.g., bark beetles (Anobium punctatum), bark beetles (Rhizopertha dominica), yellow bean weevil (Bruchidia), bean weevil (Acanthoscelides), horsetail beetle (Hypocrea), Phlebia littora (Physalis praecox), Phlebia radiata (Ebenaria), Phyllotheca brassicae (Phyllotrichia viridis), Phyllostachys nigra (Diabrotica sp.), Phyllostachys brassica (Psyllides chrysophycea), Spanish soybean beetle (Epilaphthora), Spiraria spp, Salacia sporum, Melothria brassica (Phyllospora), Rhizophora brassica, Phyllospora napus (Phyllophora), Rhizopus brassica sp, Phyllophora brassica), Rhizophora brassica sp Arachnoid species (Ptinus spp.), yellow spider beetle (niptous hololeucus), naked spider beetle (gibbsium psyllides), pseudoglutacous sp (Tribolium spp.), yellow mealworm (Tenebrio molitor), click beetle species (Agriotes spp.), broad chest click beetle species (condereus spp.), western pentacle gill tortoise (meloentha), potato gill (ampherolytica), brown new zealand gill (Costelytra zealandica), and rice root elephant (lissorophus oryzae).
From the order of the Hymenoptera (Hymenoptera), for example, the species Trichocaulon spp, the species Vespa spp, the species Lapacha spp, the species Lapeus spp, the species Melissa, the species Vespa spp.
Diptera (Diptera), for example, the species of the genus Aedes (Aedes spp.), the species of the genus Anopheles (Anopheles spp.), the species of the genus Culex (Culex spp.), the drosophila melanogaster (drosophila melanogaster), the species of the genus Musca (muscsa spp.), the species of the genus latrine (Fannia spp.), the species of the genus anthomyzidae (Calliphora erythophila), the species of the genus drosophila (Lucilia spp.), the species of the genus chrysomyzidae (chrysomyzia spp.), the species of the genus xanthocera (Cuterebra spp.), the species of the genus gastrophaea (gastrophilia spp.), the species of the genus hyponospora, the species of the genus stemysospp, the species of the genus phyllosta (ostrinia spp.), the species of the genus stemysspypspa, the species of the genus phylloxyssop (ostrea spp.), the species of the genus phyllosta (hylocera, the species of the genus phyllostigma), the species of the genus phyllosta (ostrea, the species of the genus eutherococcus (ostrinia spp.), the species (ostrinia spp.), the genus), the species of the genus phyllosta (ostrinia), the genus eutrophus spp.), the species (ostrinia spp.), the species of the genus eutrophus (ostrinia, the genus), the species of the genus eutrophus (ostrinia spp.), the genus eutrophus spp).
Siphonaptera (Siphonaptera), for example, Xenopsylla cheopis (Xenopsylla cheopis), Ceratophyllus spp (Ceratophyllus spp.).
Arachnida, for example, the species dicroti intermedia (Scorpio maurus), Tetranychus niger (Latrodectus maurus), aleurotes dermans (Acarus srorum), eurytea species (Argas spp.), aleurobia species (ornithiosos spp.), Dermanyssus gallinae (Dermanyssus gallinarum), scirpus griseus (Eriophyes ribis), lucorum citrinum (phyllocoptruvora), Boophilus species (Boophilus spp.), Rhipicephalus spp., taraxyrium species (rhipiceps spp.), alemma species (amymopsis spp.), vitrea species (hyalosporidium sp.), scleroderma species (irgastus spp.), Psoroptes sp., sargastus species (sargastus spp.), Psoroptes species (mange spyris spp.), Psoroptes species (mange sporus spp.), Psoroptes spp.), ales species (mange spp.), psorales species (mange spp.), ales spp.), psorales species (mange sp.), ales species (mange spp.), psorales species (mange, mange sp.), mange sp).
Plant parasitic nematodes include, for example, Pratylenchus spp, rhabdoid nematode (radioHolus similis), hedyotis (Ditylenchus dipsaci), hemipenetrans (Tylenchus semipenatrans), Heterodera spp (Heterodera spp), Heterodera spp (Globodera spp), Meloidogyne spp (Meloidogyne spp), Gloendoria spp (Aphelenchus spp), Ostertagia spp (Longidorus spp), Ostertagia spp (Xipehnema spp), Trichostrongylus spp (Tricodera spp), and Trichostrongylus spp (Burserenoides spp).
The active compound combinations according to the invention, which contain a compound of the formula (I) and at least one compound 1 to 15, are particularly suitable for controlling "biting" pests. In particular the following pests are included:
lepidoptera (Lepidoptera), for example, Henry diamondback moth (Pectinophoragossypiella), looper (Bupalus piniarius), winter-size moth (Cheimatobirudia), Plumbum xylostella (Lithocolletis blancardella), apple moth (Hypomeuta padela), Plutella xylostella (Plutella xylostella), yellow-brown cutworm (Malacosa neustria), yellow-moth (Euproctis chrysospora), Pothida species (Lyotricha spp.), cotton latent moth (Buccnaturaria thys), Phylophila (Phyllosticta ostrinia), Geotrichum species (Agrostis spp.), Chelidota sp., Sporida species (Sporidia sp.), Sporidia sp., Sporidia Sporida, Sporidia (Sporidia sp.), Sporidia sp., Sporidia Sporida, Sporidia (Sporidia), Sporidia, Sporidia (Sporidia) and Sporidia (Sporidia) species (Sporidia) of Sporidia, Sporidia, Sporidia (Sporidia) of Sporidia, Sporidia, Sporidia, Mediterranean meal moth (Ephemeria kuehniella), pyralidae medinalis (Galleria mellonella), Trichoplusia bissella, Bombycis mori (Tenebia pellionella), Bombycis mori (Tenebia pellioniana), Brown moths (Hofmenophila pseudostella), Linearia virescens (Cacoecia podana), Capua retena, Colostrinia furnacalis (Choristoneura furifera), grape fruit moth (Clysia ambiguella), tea leaf roller moth (Homona Cnmagnanima), oak green roller moth (Torx virgina), aphalocerus spp.
Coleoptera, such as, for example, bark beetles (Anobium punctatum), bark beetles (Rhizopertha dominica), yellow bean weevil (Bruchia obtectus), bean weevil (Acanthoscelides obtectus), longicorn beetle (Hythulius), firefly beetle (Agrocybe alba), potato beetle (Leptospora decemlineata), horseradish beetle (Edpachapo cochleariae), leaf beetle (Diabrotica spp.), rape head beetle (Psylides chrysospora), black soybean beetle (Epilachnesia varivestis), cabbage spp, and grain beetle (Oryza sativa), bark beetle sp, flower beetle (Physioderma), yellow rice beetle (Melothria spp.), yellow rice neck beetle (Melicoccus), yellow rice beetle (Melothria spp.), yellow rice beetle (Melothuria), yellow rice beetle (Melothria spp.), yellow rice beetle (corn beetle), rice husk, yellow rice husk, corn beetle, corn borer, corn borer, corn borer, corn borer, corn, Arachnoid species (Ptinus spp.), yellow spider beetle (niptous hololeucus), naked spider beetle (gibbsium psyllides), pseudoglutacous sp (Tribolium spp.), yellow mealworm (Tenebrio molitor), click beetle species (Agriotes spp.), broad chest click beetle species (condereus spp.), western pentacle gill tortoise (meloentha), potato gill (ampherolytica), brown new zealand gill (Costelytra zealandica), and rice root elephant (lissorophus oryzae).
The active compound combinations according to the invention which contain a compound of the formula (I) and at least one compound 5 to 8 are also particularly suitable for controlling "feeding" pests. In particular the following pests are included:
homoptera, for example, whitefly brassicae (Aleurodeses brassicae), whitefly cassava (Bemis tabaci), whitefly greenhouse (Trialeurodes vaporariorum), Aphis gossypii (Aphis gossypii), Aphis brassicae (Brevicornus brassicae), Cryptophycus theophylli (Cryptomyces terreus), Aphis saccharina (Aphis fabae), Aphis applanatus (Aphis sphaeroides), Aphis woolli (Eriosoma lanigerum), Aphis metschlegelii (Hyalophorus lucidus), Portugineus vitis (Phyllopteroma grandis), Portugineus vitis (Phyllopterura staphylx), Aphis gophycus (Pemphigus spp.), Aphis gramineus (Phyllophora glauca), Aphis virginosa (Phyllophora glauca), Phyllophora virginosa (Phyllophora), Phyllophora viridans (Phyllophora), Phyllophora viridis, Phyllophora viridula (Phyllophora), Phyllophora spp), Phyllophora viridula (Phyllophora), Phyllophora spp.), Eupatula (Phyllophora spp.), Eupatula spp.), Nepholus spp (Phyllophora spp.), Neurospora spp (Neurospora spp.), Neurospora spp (Neurospora spp. (Neuro, Pediculosis species (Psylla spp.).
In particular, the active compound combinations according to the invention have outstanding activity against caterpillars, beetle larvae, spider larvae, aphids and leaf-miners (leaf-mining flies).
The active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric substances.
These formulations are prepared in a known manner, for example by mixing the active compounds 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 water is used as filler, it is also possible, for example, to use organic solvents as auxiliary solvents. The following are basically suitable as liquid solvents: aromatic compounds such as xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions, mineral oils and vegetable oils; alcohols, such as butanol or ethylene glycol, and ethers and esters thereof; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents such as dimethylformamide and dimethylsulfoxide; or water.
Suitable solid carriers are:
for example, ammonium salts; crushed natural minerals, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth; and pulverized synthetic materials such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite; or synthetic inorganic and organic flour particles, as well as particles of organic materials, such as sawdust, coconut shells, corn cobs, and tobacco stalks. Suitable emulsifiers and/or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates; or a protein hydrolysate. Suitable dispersants are: such as lignin sulfite waste liquor and methyl cellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate; or natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives may be mineral and vegetable oils.
Colorants such as inorganic pigments, for example, iron oxide, titanium oxide and prussian blue; and organic colorants such as alizarin colorants, azo colorants, and metal phthalocyanine colorants; and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally contain from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90% by weight.
The active compound combinations according to the invention can be present in the commercially available formulations and in the use forms prepared from said formulations in admixture with other active compounds, for example insecticides, attractants, disinfectants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas, and substances produced by microorganisms, and the like.
It can also be mixed with other known active compounds, for example herbicides, or with fertilizers and growth regulators.
When used as insecticides, the active compound combinations according to the invention can furthermore be present in the commercially available formulations and in the use forms prepared from said formulations in admixture with synergists. The potentiators are compounds which enhance the activity of the active compounds of the invention, but which are not necessarily active themselves.
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 from 0.0001 to 1% by weight.
The compounds are used in a conventional manner, which is compatible with the form of use.
When used for controlling hygiene pests (hygene pest) and stored-product pests, active compound combinations are distinguished by excellent residual activity on wood and clay and good stability to alkali on lime substrates.
The active compound combinations according to the invention are active not only 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, autumn mites, flies (biting and sucking), parasitic fly larvae, lice, head lice, feather lice and fleas. The parasites include:
from the order of the Anoplurida, for example, the species Haemophilus, louse, pediculus (Pediculus spp.), Phtirus spp, and Phlebia spp.
Mallophaga (Mallophagida) and blunt (Amblycerina) and leptinocerana (ischrocerina), for example, louse species (Trimenopon spp.), pediculus avicularis species (Menopon spp.), louse species (Trinoton spp.), louse species (triloton spp.), buvicola spp., wereckia spp., Lepikentron spp., louse species (Damalina spp.), copula spp., and louse species (Felicola spp.).
Diptera and Pectinomales (Nematococcus) and Brachytrichina (Brachyserina), for example, the species Aedes, Anopheles, Culex, Simulus (Simulium spp.), Euschistus (Eusimulium spp.), phleum (phlebotomis spp.), Lucilia (Lutzomyia spp.), Culicoides (Culicoides spp.), Tabanus (Chrysophus spp.), Tabanus (Hybola spp.), Tabanus (Atylotus spp.), Tabanus (Haematopospp), Philomyspp, Begonia (Hybola spp.), Pilus, Spanisum, Sprenula (Hybola spp.), Musca (Musca spp.), Musca spp., Musca spp Lyssodaricus species, dermomycota species, gastromyza species (Gasterophilusspp.), pedicularis species (Hippobocaca spp.), pedicularis ovis species (Lipopepta spp.), and tick flies species (Melophagus spp.).
The order Siphonapterida, for example, the species Siphonapterida (Pulex spp.), the species Ctenocephalides (Ctenocephalides spp.), the species Ctenocephalides (Xenopsylla spp.), the species Ceratoptera.
Heteroptera (Heteropterida), for example, the genus bed bug species (Cimex spp.), the genus Nephocoris species, the genus Rephocoris species (Rhodnius spp.), the genus Nephocoris species (Panstrongylusspp.).
From the order of the Blattarida (Blattarida), for example, Blatta orientalis, Periplaneta americana, Blattella germanica, and the species of the genus Chartara (Supella spp.).
Acarina (Acacia or Acacia) and the phyla postarteria (Metastigmata) and Mesotimata, for example, species of the genus Iris, species of the genus Ornithodoros (Ornithodoros spp.), species of the genus Otobius (Otobius spp.), species of the genus Elyrifos, species of the genus Iris, species of the genus Orientorum, species of the genus Iris, species of the genus Dermacentor spp, species of Haemophysalissthorpp, species of the genus Hyalophycus, species of the genus Rhipicephalus, species of the genus Dermanyssus spp, species of the genus Railliotia spp, species of the genus Pneumothrix (Pneumoniussspp.), species of the genus Stenospora spp.
From the orders of the axyriales (actinodida) (prospectate) and the order of the acarida (acarida) (aspergilta), for example, species of the genus fagopyri (Acarapis spp.), species of the genus hemiptera (cheletella spp.), species of the genus spatholobus (cheletella spp.), species of the genus avicularia (Ornithocystis spp.), species of the genus cutworm (Myobasia spp.), species of the genus dermatophagoides spp.), species of the genus Demodex (Demodex spp.), species of the genus tsuga (Trombicula spp.), species of the genus Listrophorus spp.), species of the genus dermatophagoides spp., species of the genus Acarus spp., species of the genus Tyrophagus spp., species of the genus Tetranychus spp.
The active compound combinations according to the invention are also suitable for controlling arthropods which are harmful to agricultural livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees; other domestic animals, such as dogs, cats, cage birds, ornamental fish and so-called test animals, such as hamsters, guinea pigs, rats and mice. By controlling these arthropods, mortality and yield losses (in terms of meat, milk, wool, hides, eggs, honey, etc.) can be reduced, so that animal husbandry can be carried out more economically and more simply by using the active compound combinations according to the invention.
The active compound combinations according to the invention are used in a known manner in the veterinary field, and can be administered parenterally, for example by tablets, capsules, oral drinks, infusions, granules, pastes, pills, feed-through methods, suppositories, parenterally, for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), by implantation, nasally, for example by immersion or immersion, spraying, pouring on, dripping on, washing, dusting, and dermally by means of active compound-containing mouldings, for example collars, ear tags, tail tags, limb straps (limbs), halters, markers and the like.
For use in livestock, poultry, domestic animals, etc., the active compound combinations can be used directly in the form of preparations (e.g. powders, emulsions, suspensions) containing 1 to 80% by weight of the active compound, or diluted 100 to 10000 times, or as chemical baths (chemical dip).
Furthermore, it has been found that the active compound combinations according to the invention exhibit a strong insecticidal activity against insects which destroy industrial materials.
By way of non-limiting example, the following insects may preferably be mentioned:
beetles, for example, North American longicorn, Chlorophorus pelosis, Geotrichum chuanensis, Rhaponticus cornutus, Dendrobium pertinense, Rhaponticus mollis, Priobium carpini, Pseudolarix brennus, African meal beetle, southern meal beetle, Quercus quercus, Rhaponticus bark beetle, Trogopterous calophyllus, Rhaponticus nigra, Rhaponticus cornus, Rhaponticus bark beetle, Rhaponticus longus bark beetle, Rhaponticus bark beetle, Rhaponticus stem bark beetle, and stem bark beetle (stem bark beetle), and stem bark beetle, stem bark beetle, stem bark.
Dermaptera insects (dermaptera), for example, hornet (Sirex juvenus), big abies hornet (Urocerus gigas), big Turkey hornet (Urocerus gigas taurgus), Urocerus augur.
Termites, for example, European wood termites (Kalottermes flaviolis), Ramari termites (Cryptotermes breves), gray-spot Isotermes indocala, Euramerican white termites (Reticulitermes flavipes), Morton white termites (Reticulitermes santonensis), Nanohowu white termites (Reticulitermes sphaugus), Dalbergia damascenensis, Nematodara termites (Zoopolsis nevadensis), and Coptotermes formosanus.
Silverfish, such as tunny.
Industrial materials are understood in the sense of the present invention as non-living (non-living) materials, preferably polymers, adhesives, glues, paper and board, leather, wood products and coatings, for example.
The materials to be protected against insects are particularly preferably wood and wood products.
Wood and wood products which can be protected by the composition according to the invention or by a mixture containing said composition are to be understood as meaning, for example:
building lumber, timber beams, railway sleepers, bridge components, jetties, wooden vehicles, boxes, pallets, containers, utility poles, wooden siding (wood boarding), wooden doors and windows, plywood, particle board, joinery, or wood products commonly used in house construction or construction carpentry.
The active compound combinations can be used as such or in the form of concentrates or generally customary formulations, for example powders, granules, solutions, suspensions, emulsions or pastes.
The above-mentioned formulations can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellent, if desired drying agent and UV stabilizer, and if desired colorants, pigments and other processing aids.
Insecticidal compositions or concentrates for the protection of wood and wood products contain the active compounds according to the invention in a concentration of from 0.0001 to 95% by weight, in particular from 0.001 to 60% by weight.
The amount of the composition or concentrate used depends on the type, amount and medium of the insects. The optimum amount to be used can be determined by a series of application tests, respectively. In general, however, it is sufficient to use from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight, of active compound, based on the material to be protected.
Suitable solvents and/or diluents are organic chemical solvents or solvent mixtures and/or low-volatility oily or oil-type organic chemical solvents or solvent mixtures and/or polar organic chemical solvents or solvent mixtures and/or water and, if appropriate, emulsifiers and/or wetting agents.
The organic chemical solvents preferably used are oily or oil-type solvents having an evaporation number (evaporation number) of more than 35, a flash point of more than 30 ℃ and preferably more than 45 ℃. The water-insoluble, low-volatility, oily and oily solvent used is suitably a mineral oil or an aromatic fraction thereof or a mineral oil-containing solvent mixture, preferably white spirit, petroleum and/or alkylbenzene.
It is advantageous to use mineral oil in the boiling range from 170 to 220 ℃, petroleum solvent in the boiling range from 170 to 220 ℃, spindle oil in the boiling range from 250 to 350 ℃, petroleum and aromatic compounds in the boiling range from 160 to 280 ℃, turpentine, etc.
In a preferred embodiment, liquid aliphatic hydrocarbons boiling in the range from 180 to 210 ℃ or high boiling mixtures of aromatic and aliphatic hydrocarbons boiling in the range from 180 to 220 ℃ and/or spindle oil and/or monochloro naphthalene, preferably alpha-monochloro naphthalene, are used.
The low-volatility organic oily or oily solvent having an evaporation value higher than 35, a flash point higher than 30 ℃, preferably higher than 45 ℃, can be partially replaced by a high-volatility or medium-volatility organic chemical solvent, provided that the solvent mixture also has an evaporation value higher than 35 and a flash point higher than 30 ℃, preferably higher than 45 ℃, and said mixture is soluble or emulsifiable in this solvent mixture.
In a preferred embodiment, a part of the organic chemical solvent or solvent mixture or the aliphatic polar organic chemical solvent or solvent mixture is replaced. Aliphatic organic chemical solvents containing hydroxyl and/or ester and/or ether groups, such as glycol ethers, esters and the like, are preferably used.
The organic chemical binders used for the purposes of the present invention are synthetic resins; and/or binding drying oils (binding drying oils) known per se which are dilutable in water and/or are soluble or dispersible or emulsifiable in the organic chemical solvents used, in particular binders consisting of, or comprising: acrylic resins, vinyl resins such as polyvinyl acetate, polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenol resins, hydrocarbon resins such as indene/benzofuran resins, silicone resins, drying vegetable and/or drying oils and/or physical drying binders based on natural and/or synthetic resins.
The synthetic resin used as the binder may be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances may also be used as binders in amounts of up to 10% by weight. In addition, colorants, pigments, water repellents, odor masking agents, and inhibitors or corrosion inhibitors and the like, which are known per se, may also be used.
According to the invention, the composition or concentrate preferably contains at least one alkyd resin or modified alkyd resin, and/or a drying vegetable oil as organic chemical binder. Alkyd resins which are preferably used according to the invention have an oil content of more than 45% by weight, preferably from 50 to 68% by weight.
The above-mentioned binders may be partially or completely replaced by a fixing agent (mixture) or a plasticizer (mixture). The additive serves to prevent volatilization of the active compound and also crystallization or precipitation. The additives preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
Plasticizers come from the following chemical classes: phthalic acid esters, such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate; phosphate esters, such as tributyl phosphate; adipates, such as di (2-ethylhexyl) adipate; stearates, such as butyl stearate or amyl stearate; oleates, such as butyl oleate; glycerol ethers or high molecular weight glycol ethers, glycerol esters and p-toluenesulphonates.
Fixatives are chemically based on polyvinyl alkyl ethers, such as polyvinyl methyl ether, or on ketones, such as benzophenone and ethylene benzophenone.
Other suitable solvents or diluents, in particular water, may, if appropriate, be present as a mixture with one or more of the abovementioned organic chemical solvents or diluents, emulsifiers and dispersants.
Particularly effective wood protection is achieved by impregnation processes on an industrial scale, such as vacuum, double vacuum or pressure processes.
The active compound combinations according to the invention can be used simultaneously for protecting objects which come into contact with salt water or brackish water, such as ship hulls, screens, nets, buildings, mooring equipment and signalling systems, against fouling.
Fouling caused by sessile Oligochaeta animals, such as the family of the agriculidae (Serpulidae), and by species of the shells (shell) and Ledamorpha classes (goose mings), such as the different mings (Lepas) and Scalpellum (Scalpellum) species, or by species of the barnacles classes (Balanomorpha), such as the barnacles (Balanus) or the tortoises (polipes), increases the frictional resistance of ships, resulting in a significant increase in the running costs due to high energy consumption and additional frequent detentions in dry docks.
In addition to fouling caused by algae, such as the species nephela (echocarpus sp.) and the species ceramis (Ceramiumsp.), fouling caused by the category Entomostraka classified as sessile collectively known as the sprawl (cirripdia) (cirripta) is also of particular importance.
Surprisingly, it has now been found that the active compound combinations according to the invention have outstanding antifouling activity.
The use of heavy metals in the compounds which can be avoided by the active compound combinations according to the invention includes, for example, bis (trialkyltin) sulphide, tri-n-butylstannoic acid, tri-n-butylstannic chloride, copper (I) oxide, triethylstannic chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributylstannic oxide, molybdenum disulphide, antimony oxide, butyl titanate polymers, bismuth phenylchloride (bipyridyl) trichloride, tri-n-butylstannic fluoride, manganese vinyldithiocarbamates, zinc dimethyldithiocarbamate, zinc vinyldithiocarbamate, zinc and copper salts of 2-pyridinethiol 1-oxide, vinyldithiocarbamates (bisdimethyldithiocarbamates), zinc oxide, Copper (I) vinylbisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halide, or to significantly reduce the concentration of said compounds used.
If appropriate, the antifouling paints formulated to be ready for use may additionally comprise other active compounds, preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.
Preferred suitable components for combination with the antifouling composition of the invention are:
algicides, such as 2-tert-butylamino-4-cyclopropylamino-6-methylsulfanyl-1, 3, 5-triazine, dichlorophen (dichlorphen), diuron (diuron), endothecium (endothial), fentin acetate (fentin acetate), isoproturon (isoproturon), thidiazuron (methabenzthiazuron), oxyfluorfen (oxyfluorfen), quinoxaline (quinoclamine), and terbutrine (terbutrine);
fungicides, such as benzo [ b ] thiophenecarboxylic acid cyclohexylamide S, S-dioxide, dichlofluanid (dichlorfluanid), fluorofolpet, 3-iodo-2-propynyl butyl carbamate, tolyfluoride (tolyfluorid), and pyrroles, such as azaconazole (azaconazole), cyproconazole (cyproconazole), epoxiconazole (epoxyconazole), hexaconazole (hexaconazole), metconazole (metconazole), propiconazole (propiconazole), and tebuconazole (tebuconazole);
molluscicides such as fentin oxide, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb;
or conventional antifouling-active compounds, for example 4, 5-dichloro-2-octyl-4-isothiazolin-3-one, iodomethyylcarbamoylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazolyl, the potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide, pyridine/triphenylborane, tetrabutyldistannyloxyethylene oxide, 2, 3, 5, 6-tetrachloro-4- (methylsulfonyl) pyridine, 2, 4, 5, 6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2, 4, 6-trichlorophenylmaleimide.
The antifouling compositions according to the invention which are used contain the active compounds according to the invention in a concentration of from 0.001 to 50% by weight, in particular from 0.01 to 20% by weight.
In addition, the Antifouling compositions of the invention may contain conventional components, such as those described in Ungrer, chem.Ind.1985, 37, 730-.
In addition to the algicidal, fungicidal, molluscicidal active compounds and insecticidal active compounds according to the invention, the antifouling paints may also contain, in particular, binders.
Examples of recognized binders are polyvinyl chloride in solvent systems, chlorinated rubber in solvent systems, acrylic resins in solvent systems, in particular in aqueous systems, vinyl chloride/vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene/styrene/acrylonitrile rubbers, drying oils such as linseed oil, resin esters or modified hardening resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber (chlororinerbber), chlorinated polypropylene and vinyl resins.
The paints may, if appropriate, also contain inorganic pigments, organic pigments or colorants which are preferably insoluble in salt water. The lacquer may further contain a material which allows controlled release of the active compound, for example rosin. In addition, the lacquers may contain plasticizers, modifiers which influence the rheological properties and other conventional ingredients. The compounds of the invention or the abovementioned mixtures can also be contained in a self-polishing antifouling system.
The active compound combinations according to the invention are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces, including, for example, dwellings, factory workshops, offices, vehicle workshops (vehicle cabins) and the like. The combinations are useful in domestic insecticidal products for controlling said pests. They are active against sensitive and resistant species and all developmental stages. The pests include:
scorpion (Scorpionidea), for example, Scorpion (Buthus occidentalis).
Acarina (Acarina), for example, Pericarius persicae (Argas persicus), Pericarius pigeonensis (Argas reflexus), Dermatophagoides pteronyssinus (Bryobia ssp.), Dermanyssus gallinae, Glycyphaginus domestica (Glycyphaghagus domesticus), Ornithodorosus (Ornithodorousmoubata), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Amycotsutsugamus abhatensis (Trombiculus alfredigesis), Neutrobius aumnalis, Dermatophagoides pteronyssinus (Dermatophagoides pteroniensis), Dermatophagoides pteronyssinus (Dermatophagoides forinae).
Araneida (Aranea), for example, avicularia (Avicicularidae) and orbicularis (Araneidae).
From the order of the Cristaria (Opilions), for example, the Capricorn Scorpion (Pseudoscorpions chelifer), Pseudoscorpions chelidium, Cristaria opipes (Opilions Phalangium).
From the order of Isopoda, for example, Ctenocephalides farreri, Armadillidium vulgare.
From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus species (Polydesmus spp.).
From the order of the Chilopoda, for example, Geophilus spp.
From the order Periploca (Zygentoma), for example, Chlamydomonas species (Ctenohydropisma spp.), Chlamydomonas, Lathyridis, and Pheretima (Lepismodes inquinatus).
From the order of the Blattaria, for example, Blatta orientalis, Blattella germanica, Blattella asiatica (Blattella asahinai), Blattella maderaria, Periplaneta spp (Panchlora spp.), Periplaneta spp (Parcoblataspp), Periplanea australis (Periplaneta australiae), Periplaneta americana, Periplanea fuscogentosa (Periplaneta brunnea), Periplanea fumago (Periplaneta fuliginosa), Blatta palmaria (Supella longipalalpa).
From the order of the jumping sub-order (Saltatoria), for example, cricket.
From the order of the Dermaptera, for example, Forficula auricularia.
From the order of the Isoptera, for example, the species Coptotermes spp.
The order of rodentia (Psocoptera), for example, Lepinatus spp.
From the order of the Coleoptera, for example, bark beetle species, fur bark beetle species, long head beetle (Lathenticis oryzae), Cryptotaenia species (Nerobia spp.), arachnida species, bark beetle species, grain beetle, grain elephant (Sitophilus grandis), rice elephant (Sitophilus oryzae), corn elephant (Sitophilus zeamais), and Stegobium panicum (Stegobium panicum).
From the order of the diptera, for example, Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus), Aedes coracoid (Aedes taeniorhynchus), Anopheles species, Red-headed blowfly, high-weight horsefly (Chrysozona pluvialis), Culex quinquefasciatus (Culexquinquefasciatus), Culex pipiens (Culex pipiens), Culex pipiens (Culextarsalis), Drosophila species (Drosophila spp.), summer flies (Fannacanicularis), Musca domestica (Musca domestica), Chrysopa species, Sarcophaga carnaria, gna species, stable flies (Stomoxys lcitorians), European large mosquitoes.
Lepidoptera, for example, the small wax moth (Achroia grisella), the big wax moth, the Indian meal moth (Plodia interpunctella), the wood plug moth (Tinea cloacella), the bageworm, the veiling moth.
From the order of the Siphonaptera, for example, Ctenocephalides canis (Ctenocephacides cantis), Ctenocephalides felis (Ctenocephacides felis), human fleas (Pulex irritans), Tetranychus penetrans (Tunga pierrans), Cyanopsis volvatus (Cyanopsis cheopis).
From the order of the hymenoptera, for example, Formica fusca (Camptotus hercules), Formica fusca (Lasius fusgiosus), Formica fusca (Lasius niger), Lasius umbratus, Formica fusca spp.
From the order of the Anoplura, for example, head lice (Pediculus humanus capitis), body lice, pubic lice (Phthirus pubis).
Heteropterans, for example, tropical bed bugs (Cimex hemipterus), temperate bugs, long-range stinkbugs, and biting stinkbugs (Triatoma infestans).
The conjugate is used by: aerosol, pressureless spray (aerosol) products such as pumps and atomising sprays (atomizer sprays), automatic atomising systems, smoke generators, foams, gels, evaporator products with cellulose or polymer made evaporator tablets (evaprorator tablets), liquid evaporators, gel and film evaporators, propellant driven evaporators, unpowered (energy-free) or passive (passive) evaporation systems, moth papers, moth bags and moth gels; granules or powders; for thrown baits or for bait stations (baitstations).
All plants and plant parts can be treated according to the invention. Plants are to be understood as meaning all plants and plant populations, for example desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which are obtained by conventional breeding and optimization methods, or by biotechnological and genetic engineering methods, or by a combination of the aforementioned methods, including transgenic plants, but also including plant cultivars which are protected or not protected by plant breeder's rights. Plant parts are to be understood as meaning all parts of the ground and underground and plant organs, such as shoots, leaves, flowers and roots, examples which may be mentioned being leaves, needles, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include harvested plants, as well as vegetative and generative propagation material, such as seedlings, tubers, rhizomes, cuttings and seeds.
The treatment of plants and plant parts with the active compounds according to the invention can be carried out directly according to conventional treatment methods or can be effected according to conventional treatment methods on their environment, habitat or storage area. Such as dipping, spraying, vaporizing, atomizing (atomising), broadcasting, coating, in the case of propagation material, in particular seeds, it is also possible to apply one or more layers.
As mentioned above, all plants and parts thereof can be treated according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or plants obtained by conventional biological breeding methods, for example by crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars (genetically modified organisms) and parts thereof which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods, are treated. The terms "part", "part of a plant" or "plant part" are to be construed as above.
Particularly preferably, plant cultivars, each of which is commercially available or used, are treated according to the invention.
Depending on the plant species or plant cultivars, their location and growth conditions (soil, climate, vegetation period, nutrition), the treatment according to the invention may also produce superadditive ("synergistic") effects. Thus, for example, substances and compositions which can be used according to the invention can have a reduced application rate and/or a broadened spectrum of action and/or increased activity, improved 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, increased yield, increased quality and/or increased nutritional value of the harvested products, improved storage stability and/or processability of the harvested products, which can exceed the effects which are actually to be expected.
Preferred transgenic plants or plant cultivars (i.e.plants obtained by genetic engineering) to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly advantageous useful properties ("traits") to the plants. Examples of such characteristics are: improving plant growth, increasing tolerance to high or low temperatures, increasing tolerance to drought or to water or soil salt content, increasing flowering performance, making harvesting easier, accelerating maturation, increasing yield, increasing the quality and/or the nutritional value of harvested products, improving the storage stability and/or the processability of harvested products. Other examples of such properties to be particularly emphasized are: improving the resistance of plants to animal and microbial pests, for example to insects, mites, phytopathogenic fungi, bacteria and/or viruses, and increasing the tolerance of plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybean, potato, cotton, tobacco, oilseed rape (oil)seedrape) and fruit trees (the fruits are apples, pears, citrus fruits and grapes), particular emphasis being given to maize, soybeans, potatoes, cotton, tobacco and oilseed rape. A particularly emphasized property ("signature") is the increased resistance of plants to insects, arachnids, nematodes, helminths by forming toxins in plants, in particular toxins formed in plants by the genetic material of Bacillus thuringiensis (e.g.the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and combinations thereof; hereinafter referred to as "Bt plants"). Other properties ("traits") of particular emphasis are the improvement of the resistance of plants to fungi, bacteria and viruses by Systemic Acquired Resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and the corresponding expression of proteins and toxins. Further properties ("traits") which are 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 that confer the desired properties ("traits") can also be combined with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are the commercially available trademarks YIELD GARD
Figure C20048003617600481
(e.g., corn, cotton, soybean), Knockout
Figure C20048003617600482
(e.g., corn), StarLink
Figure C20048003617600483
(e.g., corn), Bollgard
Figure C20048003617600484
(Cotton), Nucotn
Figure C20048003617600485
(Cotton) and NewLeaf
Figure C20048003617600486
Maize varieties, cotton varieties, soybean varieties and potato varieties. Examples of plants which are tolerant to herbicides which may be mentioned are the plants which are commercially available under the trade name Roundup Ready
Figure C20048003617600487
(with glyphosate tolerance, e.g. corn, cotton, soybean), Liberty Link(tolerance to phosphinotricin, e.g. oilseed rape), IMI
Figure C20048003617600489
(imidazolinone tolerance) and STS
Figure C200480036176004810
Maize varieties (with sulfonylurea tolerance, e.g. maize), cotton varieties and soybean varieties. Plants with herbicide resistance (plants bred in a conventional herbicide-tolerant manner) which may be mentioned include the name Clearfield
Figure C200480036176004811
A commercially available variety of (e.g., corn). Of course, the above statements also apply to plant cultivars having the genetic traits described or to be developed ("traits"), which plants will be developed and/or marketed in the future.
The plants mentioned can be treated according to the invention in a particularly advantageous manner with the active compound mixtures according to the invention. The preferred ranges for the above mixtures also apply to the treatment of said plants. Particular emphasis is given to the treatment of plants with the mixtures specifically mentioned in the present invention.
The good insecticidal and acaricidal activity of the active compound combinations according to the invention can be seen from the examples below. Although the individual active compounds are less active, the combination exhibits an activity which exceeds the simple addition of the activities of the individual components.
The activity of the active compound combinations is higher than the sum of the activities of the active compounds used alone, i.e. there is a synergistic effect of the insecticides and acaricides.
The expected activity of a given combination of two active compounds can be calculated using the "Colby formula" in the following manner (see "calculation of synergistic and antagonistic effects of herbicidal combinations" s.r 15，20-22)：
If the number of the first and second antennas is greater than the predetermined number,
x is as followsmApplication rates in g/ha ormThe kill rate at ppm concentration with active compound a, expressed as a percentage relative to the untreated control,
y is whennApplication rate of g/ha ornThe kill rate at ppm concentration with active compound B, expressed as a percentage relative to the untreated control,
e is whenmAndnapplication rate of g/ha ormAndnthe kill rate at ppm concentrations using active compounds A and B, expressed as a percentage relative to the untreated control,
then the process of the first step is carried out,
<math><mrow> <mi>E</mi> <mo>=</mo> <mi>X</mi> <mo>+</mo> <mi>Y</mi> <mo>-</mo> <mfrac> <mrow> <mi>X</mi> <mo>&CenterDot;</mo> <mi>Y</mi> </mrow> <mn>100</mn> </mfrac> </mrow></math>
。
if the actual insect kill rate exceeds the calculated value, the activity of the combination is superadditive, i.e., there is a synergistic effect. In this case, the actually observed kill rate must exceed the expected kill rate value (E) calculated using the above equation.
Application examples
Example A
Aphis gossypii test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 parts by weight of an 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-containing water to the desired concentration.
Cotton leaves (gossypium hirsutum) which are heavily infested by the aphid gossypii (Aphis gossypii) are treated by immersion in a preparation of active compound of the desired concentration.
After the desired time, the percent kill was determined. 100% means that all cotton aphids are killed; 0% means that no Aphis gossypii is killed. The determined kill rate was calculated using the Colby formula (see page 47).
In this test, for example, the following active compound combinations according to the application exhibit a synergistic activity with respect to the active compounds applied alone:
table a 1: insect harmful to plant
Aphis gossypii test
Figure C20048003617600511
Measured value ═ measured activity
Calculated value ═ Activity calculated by Colby formula
Table a 2: insect harmful to plant
Aphis gossypii test
Figure C20048003617600512
Measured value ═ measured activity
Calculated value ═ Activity calculated by Colby formula
Example B
Myzus test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 parts by weight of an 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-containing water to the desired concentration.
Cabbage leaves (Brassicaoleracea) which are heavily infested by the green peach aphid (Myzus persicae) are treated by immersion in the preparation of active compound of the desired concentration.
After the desired time, the percent kill was determined. 100% means that all myzus persicae are killed; 0% means that no myzus persicae was killed. The determined kill rate was calculated using the Colby formula (see page 47).
In this test, for example, the following active compound combinations according to the application exhibit a synergistic activity with respect to the active compounds applied alone:
table B1: insect harmful to plant
Myzus test
Figure C20048003617600531
Measured value ═ measured activity
Calculated value ═ Activity calculated by Colby formula
Table B2: insect harmful to plant
Myzus test
Measured value ═ measured activity
Calculated value ═ Activity calculated by Colby formula
Example C
Horseradish beetle larva test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 parts by weight of an 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-containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are inoculated with larvae of the mustard beetle (Phaedon cochleariae) while the leaves are still moist.
After the desired time, the percent kill was determined. 100% means killing all simian diabrotica larvae; 0% means that the beetle larvae were killed. The determined kill rate was calculated using the Colby formula (see page 47).
In this test, for example, the following active compound combinations according to the application exhibit a synergistic activity with respect to the active compounds applied alone:
table C1: insect harmful to plant
Horseradish beetle larva test
Figure C20048003617600551
Measured value ═ measured activity
Calculated value ═ Activity calculated by Colby formula
Table C2: insect harmful to plant
Horseradish beetle larva test
Figure C20048003617600552
Measured value ═ measured activity
Calculated value ═ Activity calculated by Colby formula
Example D
Diamondback moth assay (resistant line)
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 parts by weight of an 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-containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are inoculated with larvae of the diamondback moth (Plutella xylostella, resistant line) while the leaves are still moist.
After the desired time, the percent kill was determined. 100% means killing all larvae; 0% means no larvae were killed. The determined kill rate was calculated using the Colby formula (see page 47).
In this test, for example, the following active compound combinations according to the application exhibit a synergistic activity with respect to the active compounds applied alone:
table D: insect harmful to plant
Diamondback moth assay (resistant line)
Figure C20048003617600571
Measured value ═ measured activity
Calculated value ═ Activity calculated by Colby formula
Example E
Spodoptera frugiperda test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 parts by weight of an 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-containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of Spodoptera frugiperda (Spodoptera frugiperda) while the leaves are still moist.
After the desired time, the percent kill was determined. 100% means killing all larvae; 0% means no larvae were killed. The determined kill rate was calculated using the Colby formula (see page 47).
In this test, for example, the following active compound combinations according to the application exhibit a synergistic activity with respect to the active compounds applied alone:
table E: insect harmful to plant
Spodoptera frugiperda test
Figure C20048003617600591
Measured value ═ measured activity
Calculated value ═ Activity calculated by Colby formula

Claims (5)

1. Compositions containing a compound of formula (I-a-4) and at least one anthranilamide of formula (II-1),
Figure C2004800361760002C1
wherein
R2Represents hydrogen or a methyl group,
R3represents C1-C4An alkyl group, a carboxyl group,
R4represents methyl, trifluoromethyl, trifluoromethoxy, fluorine, chlorine, bromine or iodine,
R5represents hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl or trifluoromethoxy,
R7represents chlorine or bromine, and is selected from the group consisting of,
R9represents trifluoromethyl, chlorine, bromine, difluoromethoxy or trifluoroethoxy.
2. The composition of claim 1, comprising the compound of formula (I-a-4) and at least one anthranilamide of formula (II-1) in a ratio of from 500: 1 to 1: 50.
3. Use of the composition according to claim 1 or 2 for controlling animal pests.
4. A process for the preparation of a pesticide, characterized in that a composition according to claim 1 or 2 is mixed with a filler and/or a surfactant.
5. Method for controlling animal pests, characterized in that a composition according to claim 1 or 2 is applied to the animal pests and/or their habitat.
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