Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-11-05
2002-09-10
Morris, Patricia L. (Department: 1612)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S114000
Reexamination Certificate
active
06448262
ABSTRACT:
BACKGROUND OF THE INVENTION
Nematode, insect and acarid pests destroy growing and harvested crops. In the United States, agronomic crops must compete with thousands of those pests. In addition, arthropod and helminth parasites cause hundreds of millions of dollars in economic damage to the livestock and companion animal sectors annually on a global basis. Arthropod parasites also are a nuisance to humans and can vector disease causing organisms in humans and animals.
In spite of the commercial pesticides, ectoparasiticides, endectocides and anthelmintics available today, damage to crops, livestock, companion animals and humans still occurs. Accordingly, there is ongoing research to create new and more effective pesticides, ectoparasiticides, endectocides and anthelmintics.
Certain azole derivatives which are useful as anti-ulcer agents are described in EP 405976-B1. However, that patent does not describe or suggest any pesticidal or parasiticidal utility for the azole derivatives described therein.
It is, therefore, an object of the present invention to provide a method for the control of helminth, nematode, insect and acarid pests and parasites.
It is also an object of the present invention to provide a method for the protection of growing and harvested crops from damage caused by nematode, insect and acarid attack and infestation.
It is a further object of this invention to provide a method for treating, controlling, preventing and protecting warm-blooded animals, fish and humans against infestation and infection by helminths, acarids and arthropod endo- and ectoparasites.
These and other objects of the present invention will become more apparent from the description thereof set forth below.
SUMMARY OF THE INVENTION
The present invention provides a method for the control of helminth, nematode, insect or acarid pests or parasites which comprises contacting said pests or parasites or their food supply, habitat or breeding grounds with a pesticidally or parasiticidally effective amount of a 2-(substituted thio)thiazolo[4,5-b]pyridine compound having the structural formula I
wherein
R is halogen, nitro, cyano, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylthio, C
1
-C
4
haloalkylthio or CO
2
R
1
;
n is 0, 1, 2 or 3;
Q is C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
7
cycloalkyl, C
3
-C
7
halocycloalkyl, C
4
-C
7
cycloalkenyl, C
4
-C
7
halocycloalkenyl,
C
1
-C
6
alkyl optionally substituted with one C
3
-C
7
cycloalkyl, C
3
-C
7
halocycloalkyl or CO
2
R
2
group,
C
1
-C
6
haloalkyl optionally substituted with one C
3
-C
7
cycloalkyl, C
3
-C
7
halocycloalkyl or CO
2
R
2
group; and
R
1
and R
2
are each independently hydrogen, C
1
-C
6
alkyl, CH
2
(C
1
-C
6
haloalkyl), C
3
-C
10
alkenyl, C
3
-C
10
haloalkenyl, a cation,
benzyl optionally substituted on the ring with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups or one to three C
1
-C
4
haloalkoxy groups, or
phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups or one to three C
1
-C
4
haloalkoxy groups; and
the agriculturally and/or pharmaceutically acceptable salts thereof.
This invention also comprises pesticidal and parasiticidal compositions containing those compounds. Advantageously, it has been found that the 2-(substituted thio)thiazolo[4,5-b]pyridine compounds, and compositions containing them, are especially useful for the control of nematode pests.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides a method for the control of helminth, nematode, insect or acarid pests or parasites which comprises contacting said pests or parasites or their food supply, habitat or breeding grounds with a pesticidally or parasiticidally effective amount of a 2-(substituted thio)thiazolo[4,5-b]pyridine compound of formula I.
Formula I compounds which are especially useful for the control of nematodes include
2-[(4,4,3-trifluoro-3-butenyl)thio]thiazolo[4,5-b]pyridine;
2-[(bromodifluoromethyl)thio]thiazolo[4,5-b]pyridine; and
2-[(difluoromethyl)thio]thiazolo[4,5-b]pyridine, among others.
The present invention also provides a method for the protection of growing plants from attack or infestation by nematode, insect or acarid pests which comprises applying to the foliage of the plants, or to the soil or water in which they are growing, a pesticidally effective amount of a 2-(substituted thio)thiazolo[4,5-b]pyridine compound of formula I.
The formula I compounds of this invention are useful for the control of plant parasitic nematodes and nematodes living freely in soil. Plant parasitic nematodes include, but are not limited to, ectoparasites such as Xiphinema spp., Longidorus spp. and Trichodorus spp.; semi-parasites such as Tylenchulus spp.; migratory endoparasites such as Pratylenchus spp., Radopholus spp. and Scutellonema spp.; sedentary parasites such as Heterodera spp., Globodera spp. and Meloidogyne spp.; and stem and leaf endoparasites such as Ditylenchus spp., Aphelenchoides spp. and Hirshmaniella spp.
The 2-(substituted thio)thiazolo[4,5-b]pyridine compounds of formula I are also useful for controlling insect and/or acarid pests. Insects controlled by the formula I compounds of this invention include, but are not limited to, Lepidoptera such as tobacco budworms, cabbage loopers, cotton boll worms, beet armyworms, southern armyworms and diamondback moths; Homoptera such as aphids, leaf hoppers, plant hoppers and white flies; Thysanoptera such as thrips; Coleoptera such as boll weevils, Colorado potato beetles, southern corn rootworms, western corn rootworms and mustard beetles; and Orthoptera such as locusts, crickets, grasshoppers and cockroaches. Acarina controlled by the formula I compounds of this invention include, but are not limited to, mites such as two-spotted spider mites, carmine spider mites, banks grass mites, strawberry mites, citrus rust mites and leprosis mites.
In practice generally about 0.1 ppm to about 10,000 ppm and preferably about 1 ppm to about 5,000 ppm of a formula I compound, dispersed in water or another liquid carrier, is effective when applied to plants or the soil or water in which the plants are growing or are to be grown to protect the plants from nematode, insect and/or acarid attack and infestation.
The 2-(substituted thio)thiazolo[4,5-b]pyridine compounds are also effective for controlling nematode, insect and/or acarid pests when applied to the foliage of plants and/or to the soil or water in which said plants are growing or are to be grown in sufficient amount to provide a rate of about 0.1 kg/ha to 4.0 kg/ha of active ingredient.
While the formula I compounds of this invention are effective for controlling nematode, insect and/or acarid pests of agronomic crops, both growing and harvested, when employed alone, they may also be used in combination with other biological agents used in agriculture, including, but no limited to, other nematicides, insecticides and/or acaricides. For example, the formula I compounds of this invention may be used effectively in conjunction or combination with pyrethroids, phosphates, carbamates, cyclodienes, endotoxin of
Bacillus thuringiensis
(Bt), formamidines, phenol tin compounds, chlorinated hydrocarbons, benzoylphenyl ureas, pyrroles and the like.
The compounds of this invention may be formulated as emulsifiable concentrates, flowable concentrates or wettable powders which are diluted with water or other suitable polar solvent, generally in situ, and then applied as a dilute spray. Said compounds may also be formulated in dry compacted granules, granular formulations, dusts, dust concentrates, suspension concentrates, microemulsions and
American Cyanamid Company
Keil & Weinkauf
Morris Patricia L.
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