Insecticidal aminothiazole derivatives

Details Insecticidal aminothiazole derivatives Insecticidal aminothiazole derivatives

2002-10-23

2004-05-18

Stockton, Laura L. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S266000, C546S270700, C548S195000, C548S198000

Reexamination Certificate

active

06737382

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel thiazole derivatives, which have insecticidal and acaricidal activity. The preparation and use, in agriculture and horticulture, of agrochemical compositions containing these novel insecticidal thiazoles are also disclosed.
2. Description of the Related Art
It is known in the art that certain thiazole derivatives such as those disclosed in U.S. Pat. Nos. 4,199,506, 4,284,426, 4,371,389, 4,437,875, 4,437,876 have herbicide antidote properties and in Japan Kokai Koho 06-25199 have fungicidal properties. Furthermore, it is known in the art that UK patent application GB 2331748 discloses 5-cyano or thiocarbamoyl thiazole derivatives and their use as insecticides, acaricides or nematocides. The present invention concerns the novel thiazole derivatives which have excellent insecticidal and acaricidal activity.
SUMMARY OF THE INVENTION
In accordance with the present invention, thiazole derivatives are provided having the formula (1):
wherein
R
1
is cyano or fluoroalkyl,
R
2
is halogen, SCN or aryl,
R
3
is H, C
1
-C
6
alkyl, SO
2
R
5
or C(O)R
6
,
R
4
and R
6
are, independently, aryl, phenylalkyl, alkyl, cycloalkyl groups, being optionally substituted by one or more of halogen, cyano, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, nitro, alkoxycarbonyl, alkylcarbonyloxy, alkylenedioxy, alkylcarbonyl, amino, alkylamino, haloalkoxy, alkylthio, alkylsulfonyl, haloalkenyl, alkoxycarbonylalkyl or alkoxycarbonylalkoxy; said aryl, phenylalkyl groups may additionally be fused to a cycloalkyl ring,
R
5
is C
1
-C
6
alkyl, haloalkyl,
X is O, S, NR
7
,
R
7
is alkyl, cycloalkyl, alkoxy, alkenylalkyloxy, alkynylalkyloxy, alkoxycarbonylalkyloxy.
The present invention is directed to agrochemical compositions comprising as an active ingredient at least one of the novel thiazole derivatives of the present invention, as well as to the use of these active ingredients or compositions for pest control, and, in particular as insecticides and acaricides useful in agriculture and horticulture.
For a better understanding of the present invention, reference is made to the following description and its scope will be pointed out in the appended claims.
DETAILED DESCRIPTION OF THE INVENTION
For purposes of the present invention the general terms used hereinabove and hereinbelow have the following meanings, unless otherwise defined:
Alkyl groups are, in accordance with the number of carbon atoms, straight-chain or branched and will typically be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-amyl, tert-amyl, 1-hexyl, or 3-hexyl. Cycloalkyl groups are generally cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Halogen and halo substituents will be understood generally as meaning fluoro, chloro, bromo, iodo, chloro, bromo, or iodo are preferred meanings in this invention. Haloalkyl can contain identical or different halogenatoms, typically fluoromethyl, difluoromethyl, difluorochlorormethyl, trifluoromethyl, chloromethyl, trichloromethyl Fluoroalkyl is generally fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, n-heptafluoroprpyl, n-nonafluorobutyl, n-undecafluoropentyl, n-tridecafluorohexyl and preferably trifluoromethyl and pentafluoroethyl.
Alkoxy is typically methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, and tert-butyloxy, methoxy and ethoxy are preferred.
Aryl is typically substituted phenyl or naphthyl, furyl, thienyl, six-membered heteroaromatic ring system such as pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl (
1,2,3-, 1,2,4
- and 1,3,5-), quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, indolinyl, isoindolinyl, five membered heteroaromatic ring such as thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, thiadiazolyl oxadiazolyl, pyrollyl, imidazolyl, triazolyl (1,2,3- and 1,2,4-), tetrazolyl, fused five membered rings such as benzofuranyl, benzothienyl, benzimidazolinyl; being optionally substituted by one or more of halogen, cyano, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, nitro, alkoxycarbonyl, alkylcarbonyloxy, alkylenedioxy, alkylcarbonyl, amino, alkylamino, haloalkoxy, alkylthio, alkylsulfonyl, haloalkenyl, alkoxycarbonylalkyl or alkoxycarbonylalkoxy.
Alkenyl and alkynyl groups preferably contain from 2 to 6, more preferably from 2 to 4, carbon atoms. They can be in the form of straight or branched chains, and, where appropriate, the alkenyl groups can be of either (E)- or (Z)-configuration. Examples are vinyl, allyl, propargyl.
The alkylenedioxy groups are optionally substituted with halogene (especially fluorine) and are such as methlenedioxy or difluoromethylenedioxy. Alkoxyalkyl is C
1
-C
4
alkoxy(C
1
-C
4
)alkyl such as methoxymethyl or ethoxymethyl.
The present invention provides the use as insecticides or acaricides of thiazole derivatives having the following formula (1):
wherein R
1
is cyano or fluoroalkyl (especially C
1
-C
4
fluoroalkyl), R
2
is halogen, SCN or aryl (especially phenyl, naphthyl, pyridinyl; being optionally substituted by one or more of halogen, alkyl, haloalkyl, alkoxy, nitro, alkylthio, or alkylsulfonyl), R
3
is H, C
1
-C
6
alkyl, SO
2
R
5
or C(O)R
6
, R
4
and R
6
are, independently, aryl (especially phenyl, naphthyl, pyridinyl, pyrimidinyl, thienyl, furyl, thiazolyl, isothiazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiadiazolyl (1,2,4, and 1,3,4), oxadiazolyl (1,2,4- and 1,3,4); being optionally substituted by one or more of halogen, cyano, alkyl haloalkyl, alkoxy, nitro, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl, amino, alkylamino, haloalkoxy, alkylthio, or alkylsulfonyl), R
5
is alkyl (especially C
1
-C
6
alkyl), haloalkyl (especially C
1
-C
6
haloalkyl), X is O, S, NR
7
, R
7
is alkyl (especially C
1
-C
6
alkyl), cycloalkyl (especially C
3
-C
6
cycloalkyl), alkoxy (especially C
1
-C
6
alkoxy), alkenylalkyloxy (especially (C
2
-C
6
)alkenyl(C
1
-C
6
)alkyloxy), alkynylalkyloxy (especially (C
2
-C
6
)alkynyl(C
1
-C
6
)alkyloxy), alkoxycarbonylalkyloxy (especially (C
1
-C
6
)alkoxycarbonyl(C
1
-C
6
)alkyloxy).
Examples of specific compounds of formula (1) which are of use as insecticides and acaricides include the compounds listed in Table 1 at the end of this disclosure.
A compound of formula (1) wherein R
2
is halogen and X is oxygen can be prepared by reacting a compound of formula (2):
with a compound R
4
C(O)Cl in the presence of an organic base such as pyridine and triethylamine, or inorganic base such as potassium carbonate and sodium hydride.
A compound of formula (1) wherein R
2
is halogen and X is sulfur can be prepared by reacting a compound of formula (1) wherein X is oxygen with phosphorous pentasulfide in a high boiling solvent such as pyridine, picoline, lutidine, or xylene, sulfolane or by reacting a compound of formula (3):
with a substituted thioamide R
4
C(S)NHR
3
in the presence of a base such as sodium hydride or sodium hydroxide.
Surprisingly, it has now been found that the novel compounds of formula (1) have, for practical purposes, a very advantageous spectrum of activities for protecting plants against insect and acarine pests, include such as Coleoptera, Diabrotica, Diptera, Homoptera and Lepidoptera, Heteroptera, Thysanoptera, Orthoptera and Acarina. The pests include those pests associated with agriculture, horticulture and animal husbandry, forestry, the storage of products of vegetable origin, such as fruit, grain, and timber, and also those pests associated with the transmission of diseases of man and animals. Examples of insect and acarine pest species which may be controlled by the compounds of formula (1) include:
Pieris brassicae
(white butterfly),
Pseudaletia separata
(rice armyworm),
Heliothis virescens
(tobacco budworm), Trialeurodes spp. (white flies),
Aedes aegypti
(mosquito), Agrotis spp. (cutworms),
Blatta orientalis
(cockroach), Anopheles spp. (mosquitos),
Chilo partellus
(maize stem borer), Culex spp. ((mosquitos),
Dysdercus fasciatus
(capsid),
Musca domestica
(housefly),

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