Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1995-10-16
2001-11-27
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
Reexamination Certificate
active
06323224
ABSTRACT:
The present invention relates to the use of known nitromethylene or nitroimino compounds as agents for combating technical materials destroying insects in order to preserve these materials.
The present invention also relates to compositions useful for combating these insects, preserving technical materials completely, i.e. not only against insects but also against fungi, bacteriae and algae and for treating soil to protect technical materials against termite infestations.
The invention furthermore relates to processes for treating technical materials and for soil treatment against termite infestations.
The compounds and their insecticidal use in the field of plant protection has already been known. Compare for example with EP-A 163855 and EP-A 192060.
Insecticidal agents and compositions of said compounds and their use to preserve technical materials completely and to treat soil against-termite infestations have not been known up to now.
Different insects are known as pests infesting technical materials so that due to serious damages caused thereby undesirable effects on living environment and cultural assets principally made of these materials have posed a social problem, urgently requiring effective controlling of the pests. Termites are known as important examples of these pests.
At present, use for combating technical materials destroying insects has been made of organophosphorus insecticides such as phoxim [0-(&agr;-cyanobenzylideneamino)0,0-diethylphosphorothioate], chloropyriphos [0,0-diethyl-3,5,6-trichloro-2-pyridylphosphorothioate], etc., as well as pyrethroides series insecticides such as permethrin [5-benzyl-3-furylmethyl-3-(2-methoxy-carbonyl-1-propenyl)-2,2-dimethylcyclopropane carboxylate], decamethrin [&agr;-cyano-3-phenoxybenzyl d,l-cis-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropane carboxylate], cypermethrin [&agr;-cyano-3-phenoxybenzyl (±) cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], fenvalerate [(RS)-&agr;-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate], cyflutrine [cyano-(4-fluoro-3-phenoxyphenyl) methyl-3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropane carboxylate].
However, the above-mentioned insecticides are unsatisfactory as far as effective concentration and the long lasting effect are concerned.
It has been found that the known compounds of the formula (I)
wherein X is NH or S,
Y is CH or N
Z is 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl,
R
1
is hydrogen or methyl, and
n is 0 or 1,
exhibit powerful insecticidal properties on material destroying insects and preferably on termites.
The compounds according to the invention of the formula (I) surprisingly exhibit an extremely strong insecticidal action on material destroying insects and the function is substantially superior to that of known insecticidal agents.
The compounds of the formula (I) can be used to preserve technical materials against insects.
In the formula (I), the individual residues have the following preferable meanings:
X is NH or S,
Y is CH or N,
Z is 2-chloro-5-pyridyl,
R
1
is hydrogen, and
n is 0 or 1.
As examples of the active substances to be used according to the invention, the following ones are particularly preferred:
1-(6-chloro-3-pyridylmethyl)-2-nitromethylene-imidazolidine,
3-(6-chloro-3-pyridylmethyl)-2-nitromethylene-thiazolidine,
1-(6-chloro-3-pyridylmethyl)-2-nitroimino-imidazolidine,
1-(6-chloro-3-pyridylmethyl)-2-nitromethylene-tetrahydropyrimidine, and
3-(6-chloro-3-pyridylmethyl)-2-nitromethylene-tetrahydro-2H-1,3-thiazine.
The active substances to be used according to the invention exhibit powerful insecticidal effects against material destroying insects.
They can therefore be used in insecticidal agents for combating material destroying insects and preserving technical materials. They can also be used for soil treatment against termite infestation.
As individual examples of technical materials preserved by means of the insecticidal agents according to the present invention the following ones can be mentioned: wood or composite wood-materials (such as pressed wood, particle board, chip board, wafer board, plywood, wood laminated material, freshly cut timber/lumber etc.), paper,leather or leather products, natural or synthetic polymers, textiles.
Preferable materials are wood or composite wood-materials.
As individual examples of insects to be combated or controled by the active substances of formula (I) according to the present invention the following ones can be mentioned:
Order Isoptera
Mastotermitidae
Kalotermitidae such as Kalotermes spp.
Cryptotermes spp. etc.
Termopsidae such as Zootermopsis spp. etc.
Rhinotermitidae such as Reticulitermes spp.
Heterotermes spp.
Coptotermes spp. etc.
Termitidae such as Amitermes spp.
Nasutitermes spp.
Acanthotermes spp.
Mikrotermes spp. etc.
Order Coleoptera
Lyctidae such as
Lyctus brunneus
etc.
Bostrychidae such as
Bostrychus capucinus
Dinoderus minutus
etc.
Anobiidae such as
Anobium punctatum
Xyletinus peltatus
Xestobium rufovillosum
Ptilinus pectinicomis
etc.
Cerambycidae such as
Hylotrupes bajulus
Hesperophanus cinereus
Stromatium fulvum
Chlorophorus pilosus
etc.
Oedemeridae
Serropulpidae
Curculionidae
Seolytida
Platypodidae
Order Hymenoptera
Siricidae such as Sirex spp.
Urocerus spp.
Formicidae such as Camponotus spp.
In the above Isopterous insects, especially, there may be mentioned as examples of termites in Japan:
Deucotermes speratus,
Coptotermes formosanus,
Glyptotermes fucus,
Glyptotermes satsumensis,
Glyptotermes nakajimai,
Glyptotermes Kodamai,
Incisitermes minor,
Neotermes koshunensis,
Cryptotermes domesticus,
Hodotermopsis japonica,
Reticulitermes miyatakei,
Odontotermes formosanus,
Nasutitermes takasagoensis,
Capritermes nitobei
and so on.
The active compounds of the general formula (I) in the present invention can be prepared into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compounds, and micro-capsules.
These formulations may be produced in a known manner, for example, by mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents, dispersing agents, and/or foam-forming agents. In the case of using water as an extender, organic solvents can, for example, also be used as auxiliary solvents.
As liquid diluents or carriers can be mentioned, for example, aromatic hydrocarbons, such as xylene, toluene and alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes and methylene chloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane or paraffins, for example, mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, as well as water.
By liquefied gaseous diluents or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, for example, aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
As solid diluents there may be used ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceus earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates.
As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
As emulsifying and/or foam-forming agents there may be used nonionic and ionic emulsifiers, such as polyoxyethy
Exner Otto
Obinata Toru
Schwamborn Michael
Sone Shinzaburo
Tsuboi Shin-ichi
Gil Joseph C.
Nihon Bayer Agrochem K.K.
Robinson Allen J.
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