Insecticidal methods using 4-amino-5-chloro-thieno[2,3-d]-pyrimidine compounds
The present invention relates to new insecticidal methods of using 4-Amino-5-chloro-thieno[2,3-d]-pyrimidine compounds of formula (I) wherein R 1 , R 2 , R 3 and A are defined as in the description. The present invention relates to insecticidal methods of applying such compounds of formula (I), and to new derivatives of compounds of formula (I).
1. A method for combating or controlling insects, arachnids or nematodes comprising contacting an insect, arachnid or nematode or their food supply, habitat or breeding grounds with a pesticidally effective amount of a 4-Amino-5-chloro-thieno[2,3-d]-pyrimidine compound of formula I or a composition comprising a compound of formula I:
wherein
R 1 is selected from the group consisting of hydrogen, halogen, formyl, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -haloalkynyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino, CN, CHNOH, CHNOCH 3 and CHNOC 2 H 5 ;
R 2 is selected from the group consisting of hydrogen, halogen, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino and di(C 1 -C 10 -alkyl)amino;
R 3 is hydrogen or C 1 -C 10 -alkyl; and
A is
wherein
R 10 is C 3 -C 10 -alkyl or C 1 -C 10 -haloalkyl;
or an agriculturally acceptable salt thereof.
2. A method for protecting crops and growing plants from attack or infestation by insects, arachnids or nematodes comprising contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of an Amino-5-chloro -thieno[2,3-d]-pyrimidine compound of formula I or a composition comprising a compound of formula I:
wherein
R 1 is selected from the group consisting of hydrogen, halogen, formyl, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -haloalkynyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino, CN, CHNOH, CHNOCH 3 and CHNOC 2 H 5 ;
R 2 is selected from the group consisting of hydrogen, halogen, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino and di(C 1 -C 10 -alkyl)amino;
R 3 is hydrogen or C 1 -C 10 -alkyl; and
A is
wherein
R 10 is C 3 -C 10 -alkyl or C 1 -C 10 -haloalkyl;
or an agriculturally acceptable salt thereof.
3. A method for protecting seeds from soil insects and seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with a 4-Amino-5-chloro-thieno[2,3-d]-pyrimidine compound of formula I or a composition comprising a compound of formula I:
wherein
R 1 is selected from the group consisting of hydrogen, halogen, formyl, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -haloalkynyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino, CN, CHNOH, CHNOCH 3 and CHNOC 2 H 5 ;
R 2 is selected from the group consisting of hydrogen, halogen, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino and di(C 1 -C 10 -alkyl)amino;
R 3 is hydrogen or C 1 -C 10 -alkyl; and
A is
wherein
R 10 is C 3 -C 10 -alkyl or C 1 -C 10 -haloalkyl;
or an agriculturally acceptable salt thereof.
4. A method for treating, controlling, preventing or protecting animals against infestation or infection by fleas, flies, mosquitoes, lice, ticks, mites and nematodes by administering to the animals a parasitically effective amount of a 4-Amino-5-chloro-thieno[2,3-d]-pyrimidine compound of formula I or a composition comprising a compound of formula I:
wherein
R 1 is selected from the group consisting of hydrogen, halogen, formyl, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -haloalkynyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino, CN, CHNOH, CHNOCH 3 and CHNOC 2 H 5 ;
R 2 is selected from the group consisting of hydrogen, halogen, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino and di(C 1 -C 10 -alkyl)amino;
R 3 is hydrogen or C 1 -C 10 -alkyl; and
A is
wherein
R 10 is C 3 -C 10 -alkyl or C 1 -C 10 -haloalkyl;
or a veterinary acceptable salt thereof.
5. The method of claim 4 , wherein R 1 and R 2 are selected, independently from one another, from the group consisting of hydrogen and C 1 -C 6 -alkyl.
6. The method of claim 4 , wherein R 10 is a branched C 3 -C 10 -alkyl.
7. The method of claim 4 , wherein R 10 is iso-propyl, sec-butyl or tert-butyl.
8. The method of claim 4 , wherein the compound is cis-(4-tert-Butyl-cyclohexyl)(5-chloro-thieno[2,3-d]pyrimidin-4-yl)-amine.
9. A 4-Amino-5-chloro-thieno[2,3-d]-pyrimidine compound of formula I-A3:
wherein
R 1 is selected from the group consisting of hydrogen, halogen, formyl, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -haloalkynyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino, CN, CHNOH, CHNOCH 3 and CHNOC 2 H 5 ;
R 2 is selected from the group consisting of hydrogen, halogen, C 1 -C 10 alkyl, C 1 -C 10 -haloalkyl, C 1 -C 10 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkylamino, and di(C 1 -C 10 -alkyl)amino;
R 3 is hydrogen or C 1 -C 10 -alkyl; and
R 10 is C 3 -C 10 -alkyl or C 1 -C 10 -haloalkyl;
or an agriculturally or veterinary acceptable salt thereof.
10. The compound of claim 9 , wherein
R 1 , R 2 are independently from one another, from the group consisting of hydrogen and C 1 -C 6 -alkyl.
11. The compound of claim 9 , wherein R 10 is a branched C 3 -C 10 -alkyl.
12. The compound of claim 9 , wherein R 10 is iso-propyl, sec-butyl or tert-butyl.
13. The compound of claim 9 , wherein the compound is cis-(4-tert-Butyl-cyclohexyl)-(5-chloro-thieno[2,3-d]pyrimidin-4-yl)-amine.
14. An agricultural or veterinary composition comprising the compound of claim 9 or an enantiomer, diastereomer or salt thereof and an inert liquid and/or solid carrier.
15. The method of claim 4 comprising orally, topically or parenterally administering or applying to the animals a parasitically effective amount of the compound of formula I or a veterinary acceptable salt thereof.
16. The method of claim 3 , wherein the compound is applied in an amount of from 100 mg to 10 kg per 100 kg of seeds.
17. The method of claim 3 , wherein the resulting plant's roots and shoots are protected.
18. A seed comprising the compound of claim 9 or an agriculturally useful salt thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.