Dyed compositions containing insecticides

Details Dyed compositions containing insecticides Dyed compositions containing insecticides

2001-11-13

2004-03-16

Levy, Neil S. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C424S405000, C424S406000, C424S409000, C514S609000, C514S625000, C514S645000, C523S122000

Reexamination Certificate

active

06706761

ABSTRACT:

The invention relates to insecticide-comprising polymer-based compositions which, in order to recognize the point in time when the insecticide is exhausted, comprise at least one dye which, after the insecticide has evaporated, turns a different colour.
WO 97/29 634 and 99/01 030 disclose insecticidal polymer-based compositions which release the active ingredient at elevated temperature and which can be processed to shaped articles (so-called vapour-producing tablets). The insecticides can be evaporated with the aid of heating devices; the application of the insecticides can thus be controlled as desired.
Dyes which indicate the depletion of the carrier of active ingredient by changing their colour have already been proposed for cellulose-based (cardboard) vapour-producing tablets. This type of dye is unsuitable for polymer-based insecticidal compositions.
One of the requirements which a dye for polymer-based insecticidal compositions must meet is that they must be capable of being distributed homogeneously in the polymer.
A further requirement which such a dye must meet is that no disadvantageous inter-actions with the insecticide result. One of the preferred insecticides of WO 97/29 634 and 99/01 030 is transfluthrin=(2,3,5,6-tetrafluorophenyl)-methyl (1R)-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate. Thus, the dye to be used in accordance with the invention should be compatible, in particular, with transfluthrin and indicate the exhaustion of the latter by a colour change. Moreover, this colour change should be drastic so that it is easy to notice.
It has now been found that o-cyanoazo dyes which comprise the unit
are outstandingly suitable for this purpose.
The invention relates to dye-comprising polymer-based insecticidal compositions, characterized in that the dye comprises at least one compound of the formula
in which
X, Y independently of one another represent CN or NO
2
and
R represents an optionally substituted aromatic radical
(with the proviso that X═Y═NO
2
must not apply).
The most important insecticides for the compositions according to the invention are pyrethroids.
The preferred pyrethroid active substances are:
1) 3-allyl-2-methyl-cyclopent-2-en-4-on-1-yl d/l-cis/trans-chrysanthemate (allethrin/Pynamin®),
2) 3-allyl-2-methyl-cyclopent-2-en-4-on-1-yl d-cis/trans-chrysanthemate (Pynamin forte®),
3) 3-allyl-2-methyl-cyclopent-2-en-4-on-1-yl d-trans-chrysanthemate (Bioallethrin®),
4) 2,3,5,6-tetrafluorobenzyl (+)-1R-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate (transfluthrin, Bayothrin®),
5) (S)-3-propargyl-2-methyl-cyclopent-2-en-4-on-1-yl (1R)-cis/trans-chrysanthemate (prallethrin/Etoc®),
or mixtures of these active substances.
Active substances which are particularly preferably used are 3-allyl-2-methyl-cyclopent-2-en-4-on-1-yl d-cis/trans-chrysanthemate (Pynamin forte®) and
2,3,5,6-tetrafluorobenzyl (+)-1R-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate(transfluthrin).
The polymer base on which the compositions according to the invention are based comprises at least one polymer with a softening range between 100 and 300° C., preferably between 150 and 250° C., in particular between 150 and 200° C.
In amorphous thermoplastic polymers, the softening range is identified by the glass transition temperature, and in semicrystalline polymers by the melting temperature.
Polymeric materials which are preferably used are amorphous and semicrystalline polymers and mixtures of these which can be processed thermoplastically, that is to say as a viscous melt, and whose softening range is below the boiling point of the active substances to be incorporated under atmospheric pressure. The polymers for the active substance in question are chosen in such a way that the active substance mixes with the polymer at least to some extent.
Suitable polymers which are preferably used are:
PVC (non-rigid), polystyrene, styrenetbutadiene, styrene/acrylonitrile, acrylonitrile/butadiene/styrene, polymethyl acrylate, amorphous polycycloolefins, cellulose esters, aromatic polycarbonates, amorphous aromatic polyamides, polyphenylene ethers, poly(ether) sulphones, polyimides, polyethylene, polypropylene, polybutylene, polymethylpentene, PVC (rigid), polyamide, polyether amides, polyester amides, polyoxymethylene, polyethylene terephthalate, polybutylene terephthalate, polyimide, polyether (ether) ketone and polyurethanes.
Examples of preferred mixtures are:
blends of polycarbonates with polybutylene terephthalate, blends of polyamide-6 and styrene/acrylonitrile, blends of polypropylene and polymethylpentene.
Particularly preferred are polypropylene, poly-4-methyl-1-pentene and mixtures of these.
The compositions according to the invention are preferably based on mixtures comprising
A. 0.1 to 80% by weight, preferably 0.2 to 40% by weight, in particular 0.5 to 20% by weight, specifically 1 to 12% by weight of transfluthrin
and
B. 99.9 to 20% by weight, preferably 99.8 to 60% by weight, in particular 99.5 to 80% by weight, specifically 99 to 88% by weight of poly-4-methyl-1-pentene which, in turn, can be replaced by another poly-&agr;-olefin to up to half, preferably up to a third, in particular up to a quarter of its weight,
the percentages in each case relating to the total of components A+B.
Transfluthrin and a process for its preparation are disclosed in German Offenlegungsschrift 37 05 224 (=European Patent Specification 279 325).
Poly-4-methyl-1-pentene B is a polymer, preferably with a glass transition temperature of 50 to 60° C., a softening temperature measured by the Vicat method (ASTM D 1525) of 140 to 180° C., preferably 170 to 175° C., and a melt-flow index (260° C./5 kg), measured in accordance with ASTM D 1238, of 20 to 200, preferably 22 to 35[g/10 min]; it is known that it can be prepared by polymerizing 4-methyl-1-pentene
Suitable poly-&agr;-olefins which can replace some of the poly-4-methyl-1-pentene are mainly polyethylenes, polypropylenes, polybutenes and polyisobutenes and copolymers of the &agr;-olefins on which the abovementioned polymers are based, such as, for example, ethylene/propylene copolymers. Preferred polypropylenes comprise iso- and/or syndiotactic polypropylenes, preferably with a softening temperature, measured by the Vicat method (ISO 306), of 130 to 170° C., preferably 140 to 160° C., and a melt-flow index (230° C./2 kg), measured in accordance with ISO 1133, of 20 to 40, preferably 25 to 35 [g/10 min].
In the event that “other” poly-&agr;-olefins are concomitantly used, the weight ratio of poly-4-methyl-1-pentene/poly-&agr;-olefins can be 70:30 to 99:1, preferably 80:20 to 95:5.
Radicals R which are suitable for the compounds of the formula (II) are radicals of coupling components of the benzene, naphthalene, indole, pyridine and tetrahydroquinoline series, but preferably N-substituted paminoaryl radicals and, in particular, anilines of the formula
In this formula,
R
1
represents hydrogen, C
1
-C
18
-alkyl, C
1
-C
18
-alkoxy, C
6
-C
16
-aryloxy, C
1
-C
12
-alkylcarbonylamino, C
6
-C
12
—Ar—C
1
-C
4
-alkylcarbonylamino, C
5
-C
12
-cycloalkylcarbonylamino, C
6
-C
15
-arylcarbonyl amino, C
1
-C
5
-heteroylcarbonylamino, C
1
-C
12
-alkoxycarbonylamino, C
1
-C
12
-alkylsulphonylamino, C
6
-C
15
-arylsulphonylamino, aminocarbonylamino, CN, CF
3
, carbamoyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
12
-alkoxycarbonyl, sulphamoyl, di-C
1
-C
6
-alkylaminosulphonyl or C
1
-C
12
-alkylsulphonyl,
R
2
represents hydrogen, C
1
-C
18
-alkyl, C
6
-C
12
—Ar—C
1
-C
4
-alkyl or C
6
-C
5
-aryl,
R
3
represents hydrogen, C
1
-C
18
-alkyl or C
6
-C
12
—Ar—C
1
-C
4
-alkyl, and
R
4
represents hydrogen, C
1
-C
18
-alkyl, C
1
-C
18
-alkoxy, C
5
-C
15
-aryloxy, C
6
-C
12
—Ar—C
1
-C
4
-alkoxy, halogen, CN, carboxyl or C
1
-C
12
-alkoxycarbonyl.
The alkyl and alkoxy radicals mentioned above in any desired context (that is to say also, for example, alkylsulphonyl or alkoxycarbonyl) are preferably to be understood as radicals having 1 to 4 C atoms which are prefe

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