AU604109B2 - 3-substituted 1-(2-chlorothiazol-5-yl-methyl)-2-nitroimino- 1,3-diazacycloalkanes - Google Patents

3-substituted 1-(2-chlorothiazol-5-yl-methyl)-2-nitroimino- 1,3-diazacycloalkanes Download PDF

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AU604109B2
AU604109B2 AU14541/88A AU1454188A AU604109B2 AU 604109 B2 AU604109 B2 AU 604109B2 AU 14541/88 A AU14541/88 A AU 14541/88A AU 1454188 A AU1454188 A AU 1454188A AU 604109 B2 AU604109 B2 AU 604109B2
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spp
methyl
substituted
nitroimino
alkyl
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AU1454188A (en
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Benedikt Becker
Bernhard Homeyer
Wilhelm Stendel
Hilmar Wolf
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

S 137432 JGS:GS 2175T/20 6Vg80
AUSTRALIA
PATENTS ACT 1952 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE Application Number: Lodged: Complete Specification Lodged: Accepted: Published: Priority: ,Related Art: <r 4,,Etr Name of Applicant: Address of Applica j Actual Inventor: Address for Servic tC TO BE COMPLETED BY APPLICANT BAYER AKTIENGESELLSCHAFT nt: D-5090 Leverkusen, Bayerwerk, Germany Hilmar Wolf Benedikt Becker Bernhard Homeyer Wilhelm Stendel ARTHUR S. CAVE CO.
Patent Trade Mark Attorneys Level Barrack Street SYDNEY N.S.W. 2000
AUSTRALIA
"3-SUBSTITUTED Complete Specification for the invention entitled- 1-(2-CHLOROTHIAZOL-5-YL-METHYL)-2-NITROIMINO-1,3-DIAZACYCLOALKANES".
The following statement is a full description of this invention including the best method of performing it known to me:- This document contains the amendments made under Section 49 and is correct for printing 1 ASC 49 i The present invention relates to new 3-substituted 1-(2-chloro-thiazol-5-yl-methyl)-2-nitroimino-1,3diazacycloalkanes, a process for their preparation and their use in agents for combating pests, in particular as insecticides.
It is already known that certain organic nitro compounds, such as, for example, 2-nitromethylene-2Htetrahydro-1,3-thiazine, have insecticidal properties (compare U.S. Patent Specification 3,993,648).
The new 3-substituted 1-(2-chloro-thiazol-5-ylmethyl)-2-nitroimino-1,3-diazacycLoalkanes of the general formula (I) Cl "S CH2 (1)
N-
(CH2)n
NO
2
N--
R
in which n represents the numbers 0 or 1 and R represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, C 5
-C
20 -alkyl, C 3
C
10 -alkenyl or C 3
-C
10 -alkinyl, or represents one of the groupings -CH-R 1
-COR
2
S(
one of the groupings -CH2-R -COR -S(O)m-R 00 t ooo00 0 0 o 00 0 0 4 ooo i c 0 0 C(ri
C
LLC(
r~rooc r L E
OR
4 -p II 0 OR wherein
R
1 represents in each case an optionally substituted radical from the series comprising phenyl, pyridyl, furyl, thienyl and thiadiazolyl and
R
2 represents methyl with the proviso that n then represents 0 or represents optionally sub- Le A 25 153 la stituted C 2
-C
2 0 -aLkyl, optionally subF.ituted
C
3
-C
6 -cycloakyl, optionally substituted C 2
-C
20 alkenyL or optionaly substituted phenyL, or represents methoxy, C 3
-C
20 -akoxy, benzyLoxy or phenoxy, m represents the numbers 0, 1 or 2, R represents optionally substituted g 1
-C
20 alkyL, or represents optionally substituted phenyl, Q represents oxygen or sulphur and 4 R and R represent Cl-C 4 -aLkyl, have now been found.1 op i n Preferred possible substituents for optionally substituted phenyl are: halogen, cyano, nitro, C 1 C4-alkyL, trifluoromethyl, C 1
-C
4 -akoxy and Cl-C 4 alkoxy-larbonyl.
Preferred possible substituents for R optionally substituted pyridyl are: halogen, cyano, nitro, C 1
C
4 -alkyL, trifluoromethyl, C 1
-C
4 -akoxy and C 1
-C
4 alkoxycarbonyl.
1 Preferred possible substituents for R optionally substituted furyl, thienyl, thiazolyl or thiadiazolyl are: halogen, Cl-C 4 -aky and C 1
-C
4 -haogenoakyl.
Preferred possible substituents for R optionally substituted C 2
-C
20 -alkyl are: halogen, cyano and
C
1
-C
4 -akoxy.
Preferred possible substituents for R 2 optionally substituted C 3
-C
6 -cycloalkyl are: halogen and
C
1
-C
4 -akyl.
Preferred possible substituents for R 2 optionally substituted C 2
-C
20 -alkenyl are: halogen.
ally 2 Preferred possible substituents for R optionally substituted phenyl are: halogen, Cl-C 4 -akyl, trifluoromethyl, cyano, nitro, C 1
-C
4 -akoxy and C 1
-C
4 alkoxycarbonyl.
3 Preferred possible substituents for R option- Le A 25 153 -2aL~y substituted Cl-C 20 -aLkyL are: ha~ogen.
Preferred possibLe substituents for R 3 =optionaLLy substituted phenyL are: haLogen, Cl-C 4 -aLkyL, trifLuoromethyL, cyano, nitro, Cl-C 4 aLkoxy and Cl-C 4 aLkoxycarbonyL.
It has furthermore been found that the new 3substituted 1-(2-chLoro--thiazoL-5-yL-nethyL )-2-nitroimino-1,3-diazacycLoaLkaies of the generaL formuLa (1) are obtained by a process in which 1-(2-chLoro-thiazoL-5yL-methyL )-2-nitroimino-1,3-diazacycLoaLkanes of the generaL formuLa (II)
NO
2
H
II Vat 'Vat a' a a Via' a al a aaaat a t in which n has the abovementioned meaning, 15 are reacted with haLogen compounds of the generaL formuLa (III) 4? V V a at a at
U'
lata X- R (I II in which R has the abovementioned meaning and X represents haLogen, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diLuent.
The new 3-substituted 1-C2-chLoro-thiazoL-5-yLmethyl )-2-nitroirnino-1,3-diazacycioaLkanes of the formuLa are distinguished by a high activity as insecticides.
SurprisingLy, the compounds of the formuLa according to the invention exhibit a considerabLy more powerful insecticidal action than organic nitro compounds of comparabLe structure and action profiLe, such as, for Le A 25 153 -3- .i i_ 4., 4'( 4I 4.( exampLe, 2-nitromethylene-2H-tetrahydro-1,3-thiazine.
The invention preferably relates to compounds of the formuLa in which n represents zero and R represents methyl, ethyl, propyl, isopropyl, butyL, isobutyl, sec-butyL or C 5
-C
18 -a kyL, or represents C 3
-C
6 -alkenyL or c 3 -c 4 -aLkinyl, or represents the grouping -CH2-R
I
in which R1 represents phenyl [which is optiontlLy substituted by fluorine, chlorine, methyl, methoxy or C 1
-C
2 -alkoxy-carbonyl], pyridyl [which is optionally substituted by chlorine or methyl] or furyl, thienyL or thiazoLyl [which are optionally substituted by chlorine or methyl], and in which, furthermore, R represents the grouping -CO-R in which
R
2 represents C 1
-C
18 -alkyl, C 2
-C
18 -akenyl, phenyl Ewhich is optionally substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, cyano, nitro or methoxyl or C 3 -Cg-akoxy, and in which, furthermore, 25 R represents the grouping -S0 2 -R in which
R
3 represents C 1
-C
8 -alkyl [which is optionally substituted by fluorine or chlorine] or phenyl [which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyL, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy and/or C1-C 2 -akoxy-carbonyL], and in which, furthermore, '4i( 4 4 U 4. 4 R represents the grouping
Q
ll,_-R4
R
Le A 25 153 4 in which Q represents oxygen or sulphur and R and R 5 represent C 1
-C
3 -aLkyl.
If, for example, 1-(2-chloro-thiazot-5-yL-methyl)- 2-nitroimino-imidazolidine and propargyL bromide are used as starting substances for carrying out the preparation process according to the invention for the compounds of the formula the reaction of these compounds can be outlined by the foLLowing equation:
N-
CI S CH2-N NH Br-CH 2
-COCH
NO
2 HBr
H
2 N.NC 2
-CECH
N
N02 fIg I I a t 1111
II
'''elf S.1.
o a a I I I Formula (II) provides a general definition of the 1-(2-chloro-thiazoL-5-yL-methyL)-2-nitroimino-1,3-diazacycloalkanes to be used as starting substances in the preparation process according to the invention. In this formula, n preferably represents zero. 1-(2-Chlorothiazol-5-yl-methyl)-2-nitroimino-imidazoLidine is thus preferred as the starting compound of the formula (II).
The starting substances of the formula (II) are 20 already known (compare European Patent A-192,060).
Formula (III) provides a general definition of the halogen compounds furthermore to be used as starting substances. In this formula (III), R preferably represents those radicals which have already been mentioned as preferred for R in connection with the description of the substances of the formula according to the invention, and X preferably represents chlorine or bromine.
Examples which may be mentioned of the starting substances of the formula (III) are: Le A 25 153 5 [riethyL, ethyl, propyL, isopropyL, butyL, isobutyt, sec-butyL, pentyL, isopentyL, sec-pentyL, hexyL, octyt, decyL, dodecyL, hexadecyL and octadecyL chLoride and bromide, aLLyL, crotyL and propargyL chloride and bromide, benzyL, 4-fLuoro-benzyL, 4-chLoro-benzyL, 2chLoro-benzyL and 4-methyL-benzyL chloride and bromide, 2-ch Loro-5-ch Loro-methyl-pyr idine, 2-ch Loro-5-ch LanarethyL-thiazoLe, acetyL chLoride, propionyL and butyry.
chLoride, pentanoyL, hexanoyl, octanoyL, decanoyL, dodecanoyL, tetradecanoyL, hexadecanoyL and octadecanayt chLoride, acrylyL and crotyL chLoride, benzoyL, 4-fLuarobenzoyL, 4-chLoro-benzoyL, 4-nitro-benzoyL and 4-me'thyLbenzoyL chLoride, propyL, butyL, pentyL, hexyL, heptyL and octyL chioro-formate, methane-, ethane-, chioromethane-, trifLuoromethane-, tetrafLuorobutane- and perfLuorooctane-suLphonyL chloride, benzene-, 2-fLuorobenzene-, 2-chLoro-benzene-, 4-chLoro-benzene-, dichLoro-benzene-, 2-bromo-benzene, 2-cyano-benzene-, Sol, 2-nitro-benzene-, 4-ni tro-benzene-, 2-trifLuoromethyLbenzene-, 2-methyL-benzene-, 4-methyL-benzene-, 2-methoxydofbenzen 2-d i fLu or ome tho xy-ben zen 2- tr if Iuo rome tho xy- CCC benzene-, 4-trif Luoromethoxy-benzene-, 2-methoxycarbonyLbenzene-, 4-methoxycarbonyL-benzene-and 2-ethoxyca rbonyL- 4 benzene-suLphonyL chloride, phos-phoric acid chLoridedimethyl ester and -diethyL ester and thiophosphoric acid CCC chLonide-dimethyL ester and -diethyL ester.
The starting substances of the formula (111) are known chemicaL compounds.
The process according to the invention for the preparation of the new compounds of the formuLa is preferably carried out using diLuents. Possible diluents C C here are virtually all the inert organic solvents. These include, preferably, aLiphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cycLohexane, petroleum ether, benzine, Ligroin, benzene, toLuene, xyLene, methyLene chloride, ethylene Le A 25 153 -6- Li chloride, chloroform, carbon tetrachoride, chlorobenzene and o-dichlorobenzene, ethers, such as diethy ether, dibutyL ether, glycol dimethyL ether, digLycoL dimethyl ether, tetrahydrofuran and dioxane, ketones, such as S acetone, methyL ethyL ketone, methyl isopropyL ketone and methyl isobutyL ketone, esters, such as methyL and ethyL acetate, nitriles, such as, for exampLe, acetonitrile and propionitriLe, amides, such as, for example, dimethyliormamide, dimethylacetamide and N-methyLpyrroLidone, and dimethyLsulphoxide, tetramethylene sulphone and
V
hexamethylphosphoric acid triamide.
Acid acceptors which can be used in the process according to the invention are aLL the acid-binding agents which can usually be employed for such reactions.
Preferred possible acid-binding agents are alkali metal hydrides, such as, for example, sodium hydride, alkali metaL hydroxides, such as, for example, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, such as, for example, calcium hydroxide, alkali metal carbonates and alcoholates, such as sodium carbonate, potassium carbonate, sodium methylate or ethylate and potassium methylate or ethylate, and furthermore aLiphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethytbenzylamine, pyridine, 1,5-diazabicyclo-E4,3,0]-non-5-ene (DBN), 1,8-diazabicyclo-[5,4,0J-undec-7-ene (DBU) and 1,4-diazabicyco-C2,2,2-octane
(DABCO).
The reaction temperatures can be varied within a substantial range in the process according to the invention. The reaction is in general carried out at temperatures between OOC and 150 0 C, preferably at temperatures between 10 0 C and 1000C.
The process according to the invention is in generaL carried out under atmospheric pressure.
For carrying out the process according to the invention, the starting substances of the formulae (II) Le A 25 153 7 and (III) are in general empLoyed in approximateLy equimoLar amounts. The starting substances are in general mixed with the acid acceptor and the diLuent at room temperature and the reaction mixture is stirred at the stated reaction temperature until the reaction has ended.
Working up can be carried out by customary methods.
The active compounds are suitabLe for combating animaL pests, preferabLy arthropods and nematodes, in particular insects and arachnids, encountered in agricuLture, in forestry, in the protection of stored products and of materiaLs, and in the hygiene field. They are active against normaLLy sensitive and resistant species and against aLL or some stages of development. The abovementioned pests include: From the order of the Isopoda, for example, Oniscus aseLLus, ArmadiLLidium vuLgare and PorceLLio scaber. From the order of the Diplopoda, for exampLe, BLaniuLus guttulatus. From the order of the Chilopoda, for exampLe, Geo- 2 phiLus carpophagus and Scutigera spec. From the order of the Symphyla, for example, Scutigerella immacuLata. From the order of the Thysanura, for exampLe, Lepisma saccharina, From the order of the Collembola, for example, Onychiurus armatus. From the order of the Orthoptera, for exampLe, Blatta orientaLis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, GryLLotatpa spp., Locusta migratoria migratorioides, MeLanopLus differentialis and Schistocerca gregaria. From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example, Reticulitermes spp..
From the order of the-Anopura, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp. From the order of the Mallophaga, for example, Trichodectes spp. and DamaLinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus Le A 25 153 -8- 'intermedius, Piesma quadrata, cimex 1LectuLarius, Rhodrwius proLixus and Triatoma spp. From the order of the Homoptera!f for exampLe, ALeurodes brassicae, Bemisia tabaci, TriaLeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, cryptomyzus ribis, Aphis fabae, DoraLis pomi, Eriosorna Lanigerum, HyaLopterus arundinis, Macrosiphum avenae, Myzlus spp., Phorodon humuLi, RhopaLosiphum padi, Ernpoasca spp., EusceLis biLobatus, Nephotettix cincticeps, Lecanium corni, t Saissetia oLeae, LaodeLphax striateLLus, NiLaparvata Lugens, AonidieLLa aurantii, Aspidiotus hederae, Pseudococcus spp.
and PsyLLa spp. From the order of the Lepidoptera, for example, Pectinophora gossypieLLa, BupaLus piniarius, Cheimatobia brumata, LithocoLLetis bLancardeLLa, Hyponomeutta padeLLa, PLuteLLa macuLipennis, MaLacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. BuccuLatrix thurberieLLa,, PhyLLocnistis citreLLa, Agrotis spp., Euxoa spp., FeLtia spp., Earias insuLana, HeLiothis spp., Spodoptera exigua, Mamestra brassicae, PanoLis fLammea, Prodenia Litura, Spodopotera spp., TrichopLusia ni, Carpocapsa pomoneLLa, Pieris spp., ChiLo spp., Pyrausta nubiLaLis, Ephestia kuehnieLta, GaLLeria meLLoneLLa, TineoLa bisseLLieLLa, Tinea peLLioneLta, HofmannophiLa pseudospreteLLa, Cacoecia podana, Capua retifl cuLana, Choristoneura fumiferana, CLysia ambigueLLa, Homona 4 magnanima and Tortrix viridana. From the order of the CoLeoptera, for exampLe, Anobium punctatum, Rhizopertha U dominica, AcanthosceLides obtectus, AcanthosceLides obtectus, HyLotrupes bajuLus, AgeLastica aLni, Leptinotarsa decem- Lineata, Phaedon cochLeariae, Diabrotica spp., PsyLLiodes chrysocephaLa, Epilachna varive stis, Atomaria spp., OryzaephiLus surinarnensis, Antho nomus spp., SitophiLus spp., Otiorrhynchus sulcatus, CosmopoLites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., MeLi-, gethes aeneus, Ptinus spp., Niptus hoLoLeucus, Gibbium psyLLoides, TriboLium spp., Tenebria moLitor, Agriotes spp., Cono derus spp., MeLoLontha meLoLontha, AmphimaLLon soLsti- Le A 25 153 -9tialis and Costelytra zeaLandica. From the order of the Hymenoptera, for example, Diprion spp., HopLocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp. From the order of the Diptera, for example, Aedes spp., AnopheLes spp., CuLex spp., DrosophiLa meLanogaster, Musca spp., Fannia spp., CaLLiphora erythrocephaLa, LuciLia spp., Chrysomyia spp., Cuterebra spp., GastrophiluS spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, OscineLLa frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oLeae and TipuLa paludosa. From the order of the Siphonaptera, for exampLe, XenopsyLLa cheopis and CeratophyLLus spp.
From the order of the Arachnida, for exampLe, Scorpio maurus and Latrodectus mactans. From the order of the Acarina, for exampLe, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gaLLinae, Eriophyes ribis, PhyLLocoptruta oLeivora, Boophilus spp., RhipicephaLus spp., AmbLyomma spp., HyaLomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., and Tetranychus spp..
The phytoparasitic nematodes incLude PratyLenchus spp., Radopholus similis, DityLenchus dipsaci, TyLenchu- Lus semipenetrans, Heterodera spp., MeLoidogyne spp., ApheLenchoides spp., Longidorus spp., Xiphinema spp. and Trichodorus spp..
The active compounds of the formuLa according to the invention are distinguished by an outstanding insecticidal activity. They have an outstanding action, in particuLar, when used as leaf insecticides and soil insecticides, against for example against rice cicadas (for example Nephotettix cincticeps), against leaf aphids (for example Myzus persicae) and against beetle Larvae (for example Phaedon cochleariae).
The active compounds of the formula according to the invention are also suitable for combating arthropods which infest agricultural stock animals, such as, Le A 25 153 for example, cattle, sheep, goats, horses, pigs, asses, camels, buffalo, rabbits, chickens, turkeys, ducks, geese and bees, other pets, such as, for example, dogs, cats, canaries and aquarium fish, and so-called experimental animals, such as, for example, hamsters, guineapigs, rats and mice. By combating these arthropods, fatalities and reductions in yield (in meat, milk, wool, hides, eggs, honey and the like) are said to be reduced, so that more profitable and simpler animal husbandry is possible by using the active compounds according to the invention.
In the veterinary sector, the active compounds according to the invention are used in a known manner by enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes and boli, of the feed-through process or of suppositories, by parenteral administration, such as, for example, by injections (intramuscular, subcutaneous, intravenous, 0° intraperitoneal and others) or implants, by nasal adminisoo tration, by dermal use in the form of, for example, dipp- 00 20 ing or bathing, spraying, pouring on and spotting on, 0o 0o washing or dusting and with the aid of shaped articles Scontaining the active compound, such as neck collars, ear o tags, taiL tags, Limb tapes, halters, marking devices and 11 the Like.
0 25 Depending on their particular physical and/or chemical properties, the active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating Ti compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans, fumigating coils and the like, as well as ULV cold mist and warm mist formulations.
These formulations are produced in known manner, for example by mixing the active compounds with extenders, Le A 25 153 11 that is, Liquid solvents, Liquefied gases under pressure, and/or solid carriers, optionally with the use of surfaceactive agents, that is emulsifying agents and/or dispersing agents, and/or foam-forming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As Liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic 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, strongly polar solvents, such as dimethylformamide and dimethylsulphoxiae, as well as water; by Liquefied gaseous extenders or carriers are meant Liquids which are gaseous at atmospheric temperature and under atmospheric pressure, for example aerosol propellant, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly dispersed silicic acid, alumina and silicates; as solid carriers for granules there are suitable: for example 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 i and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, fnr example alkylaryL polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysation products; as Le A 25 153 12 0 0 I I i 0 t t i i 1 00 a Sa flC O 0 aoa t 0000 00 dispersing agents there are suitable: for example Ligninsulphite waste liquors and methylceLLulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic.phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and The active compounds can be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, baits, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for 25 example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms, inter alia.
The active compounds can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents. Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
The active compound content of the use forms prepared from the commercially available formulations can Le A 5 153 13 I a~4a a r~c-j c 1 vary within wide Limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
The compounds are employed in a customary manner appropriate for the use forms.
When used against hygiene pests and pests of stored products, the active compounds are distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
Preparation Examples Example 1 Cl/ CH -N sN-CH- I>-C1
NO
2 a t fIll A mixture of 3.1 g (0.012 mol) of 1-(2-chlorc- 15 thiazol-5-yl-methyl)-2-nitroimino-imidazolidine, 1.9 g 0'00 (0.012 mol) of 4-chloro-benzyl chloride, 1.6 g (0.012 0000 Smol) of potassium carbonate and 50 ml of acetonitrile is heated under reflux for four hours, with stirring. After cooling, the mixture is filtered and the solvent is dis- S 20 tilled off from the filtrate under a waterpump vacuum.
The residue which remains is stirred with 50 ml of diethyl ether and the product obtained as crystals is isolated by filtration with suction.
3.65 g (79% of theory) of 1-(2-chloro-thiazol-5yl-methyL)-2-nitroimino-3-(4-chloro-benzyl)-imidazoLidine of melting point 96 0 C are obtained.
The compounds of the formula Listed in the following table can be prepared analogously to Example I and in accor.dance with the general description of the preparation process according to the invention.
Le A 25 153 14
I
(C
2 )n
NO
2 N-1 (1) Tab~e: Other examples of compounds of the formuLa (1) ExampLe MeLting point No.
~I4I 144 I It I I o -CH 2
S~
I -CM 2 SflNC 1 o -CH 2
-CH=CH
2 I -CH 2 -CH=CNi 2 1 -CH 2 >c 1 0 -,S0 2
-CH,:
I -S0 2
-CH
3 O -co-CM 3 I -CO-CM 3 0 O -F COc 2 HS 2 165 163 124 103 C 0 C C
C)
2 C114- NMR-Signal 'for C1A,-S, Le A 25 153 1. TabLe Continuation MELTING POINT (0cC) EXAMPLE No.
n -P 0 11 -P(0C 2
H
5 )2 -Ca- (CM 2 10 -C-f? -Ca- (CH 2 1 -C f 3
-(CH
2 11
-CH
3
(OH
2 11- -Ca- (CM 2 16 -i 3 -Ca- (CH 2 16
-CH
3 -COO- (CH 2 )7-CH 3
-COO-(CH
2 7
-CH
3
-CH
2
-CECH
-CH-CECH,
101 124 73 t t 0 -CH 2 0 -CH 2 -f~2 0 -CH 2
-CH=CH-CH
3 o 0 c -C r Le A 25 153 -16 TabLe -Continuation M ELTING POINT EXAMPLE No. n -R( 0
C)
0 /c 0~ LI31 0 -Cc 32 0 -c
H
33 0 -C2CH 34 0 -S0 2
-CH-
2 Ci 0 -50 2
CF
3 36 0 -C0-CH(CH 3 37 0 c0 c 4 H 39 0 -CH 3 0 2H 41. 0 -CHC(CH 3 2 42Z 0 -CH -CH(CH 3 43 0 -C 5
H
11 K44. 0 '-C 6
H
1 0 -cCOCc 4
H
9 Le A 25 153 17 'fabLe -continuation hi MELTING POINT EXAMPLE No. n R(0 C) Cl 46 0 c I 47 0 DC-H 2 49c 0 0 -SO I 51, 0 <2 1 0 0 52 S9 Le A 25 153 18 Use Examples The compound shown beLow is empLoyed as the comparison substance in the use exampLes which foLLow, r-m C
NOZ
-NitromethyLene-ZH-tetrahydro-1,3-thiazine (compare U.S. Patent Specification 3,993,648),.
12122 2221 2 '2 222 2222 2*21 2*2222 1 22 I I 2 22 I 22 2 2 C Le A 25 153 19- I f Example A Nephottettix test Solvent: 7 parts by weight of dimethyLformamide EmuLsifier: 1 part by weight of alkylaryL poLygLycoL ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Rice seedlings (Oryza sativa) treated by being dipped into the preparation of active compound of the desired concentration and are infested with the green rice cicada as Long as the seedlings are still moist.
After the specified period of time, the destruction in is determined. 100% means that all the cicadas have been killed; 0% means that none of the cicadas have been killed.
In this test, for example, the compounds obtained according to Preparation Examples S' 20 (15) and (21) show an action of 70% 100% after 6 days at an active compound concentration of 0.0001%, whereas comparison substance shows an action of onLy Le A 25 153 20 Example B Myzus test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Cabbage leaves (Brassica oleracea) which have been i heavily infested with the peach aphid (Myzus persicae) are treated by being dipped into the preparation of active compound of the desired concentration.
After the specified periods of time, the destruction in is determined. 100% means that aLL the aphids have been killed; 0% means that none of the aphids have been ki!.led.
In this test, for example, the compounds obtained according to Preparation Examples (11) and (13) show an action of 60% 90% after 1 day at an active compound concentration of 0.001%, whereas comparison substance shows an action of only it Ilt Le A 25 153 21 c j I r Example C Critical concentration test root-systemic action Test insect: Phaedon cochleariae Larvae Solvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polygLycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emuLsifier is added and the concentrate is diluted with water to the desired concentration.
The preparation of active compound is intimately mixed with soil. The concentration of the active compound in the preparation is of practically no importance, only the amount by weight of active compound per unit volume of soil, which is given in ppm mg/l), being decisive. The treated soil is filled into pots and these are planted with cabbage (Brassica oleracea). The active compound can in this way be taken up from the soil by the roots of the plants and be transported into the leaves.
To demonstrate the root-systemic effect, exclu- ,.sively the leaves are infested with the abovementioned test animals after 7 days. After a further 2 days, the evaluation is made by counting or estimating the dead animals. The root-systemic action of the active compound is deduced from the mortality figures. It is 100% if all ,,test animals have been killed and 0% if just as many test insects are still alive as in the case of the untreated control.
In this test, for example, the compounds obtained a 30 according to Preparation Examples (15) and (17) show an action of 100% at an S active compound concentration of 20 ppm, whereas comparison substance shows no detectable action.
Le A 25 153 22 Example D Critical concentration test root-systemic action Test insect: Myzus persicae Solvent: 3 parts by weight of acetone EmuLsifier: 1 part by weight of aLkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emuLsifier is added and the concentrate is diluted with water to the desired concentration.
SThe preparation of active compound is intimately mixed with soil. The concentration of the active compound in the preparation is of practically no importance, only the amount by weight of active compound per unit volume of soil, which is given in ppm mg/L), being decisive. The treated soil is filled into pots and these are planted with cabbage (Brassica oleracea). The active compound can in this way be taken up from the soil by the roots of the plants and be transported into the Leaves.
To demonstrate the root-systemic effect, exclusively the Leaves are infested with the abovementioned test animals after 7 days. After a further 2 days, the evaluation is made by counting or estimating the dead animals. The root-systemic action of the active compound is deduced from the mortality figures. It is 100% if all test animals have been killed and 0% if just as many test insects are still alive as in the case of the untreated control.
In this test, for example, the compounds obtained 1 30 according to Preparation Examples (17) and (19) show an action of 100% at an active compound concentration of 20 ppm, whereas comparison substance shows no detectable action.
i Le A 25 153 23 Example E Test'with Lucilia cuprina resistant Larvae Emusifier: 35 parts by weight of ethylene gLycoL monomethyL ether 35 parts by weight of nonyLphenol polyglycoL ether To produce a suitable preparation of active compound, three parts by weight of active compound are mixed with seven parts by weight of the abovementioned solvent mixture and the concentrate thus obtained is diluted with water to the particular desired concentration.
S 15 About 20 Lucilia cuprina res. larvae are intro- 3 duced into a test tube which contains approx. 1 cm of horse muscle and 0.5 mL of the preparation of active compound. After 24 hours, the degree of destruction is determined.
In this test, for example, the floowing compounds from the Preparation Examples show a superior action in comparison with the prior art: (19) and (21).
NOTE: The foregoing description is substantially as originally lodged and has been retained in this form to preserve the fullness of the initial disclosure, and (ii) for purposes of comparison. The scope of the invention is as defined in the proposed amended claims immediately below.
Le A 25 153 -24c

Claims (5)

1. 3-Substituted 1-(2-chlorothiazol-5-yl-methyl nitroimino-l,3--diazacycloalkanes of the general formula (1) 2 NOC H R in which n represents 0 Rrepresents C 9-c 1- alkyl, C 3-C 6-olkenyl or represents one of the groupings -CH 2 -R CO-R 3 -so 2-R or 0aO 4 wherein R represents phenyl substiLtuted by Cl or thiazolyl substituted by Cl, R 2represents C C alkyl, C c alkyl, phonyl 1 4 8 18 substituted by Cl or represents C 5-C 8-alk-xy, R 3represents C 1-C 4-alkyl, and Rand R 5represent C,-C 3-alkyl.
2. Process for the preparation of 3-substituted l-C2-chloro- thiazol 5-yl-methyl )-2-nitroimino-± 3-diazacycloalkanes of the V general formula (I) 2 R 1 2 3 4 in which n, R, R ,R ,R R and R are as defined in claim 1, characterized in that 1 J methyl)-2--nitroimino-l,3-diazacyclo-alkanes of the general formula (II) N I C CA No 2 016 Sc: DW in which n has the abovementioned meaning, are reacted with halogen compounds of the general formula (III) X R (III) in which R has the abovementioned meaning and X represents halogen, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.
3. Agents for combating pests, characterized in that they 0 0 a O*o" contain at least one 3-substituted 1-(2-chlorothiazol-5-yl- o Eo o 0 methyl )-2-nitroimino-l,3-diazacycloalkane of the formula 0 as set forth in claim 1, in admixture with extenders and/or o surface active agents. o 0
4. Method of combating animal pests, characterized in that 3-substituted l-(2-chloro-thiazol-5-yl-methyl)-2-nitroimino- 1,3-diazacycloalkanes of the formula as set forth in claim 1, are applied to animal pests and/or their environment.
5. Process for the preparation of agents against animal pests, characterized in that 3-substituted l-(2-chloro-thiazol- 5-yl-methyl)-2-nitroimino-1,3-diazacycloalkanes of the formula as set forth in claim 1, are mixed with extenders and/or surface-active agents. DATED this 23rd day of August, 1990. BAYER AKTIENGESELLSCHAFT By Its Patent Attorneys ARTHUR S. CAVE CO. LIJ T 0 26 0165c:DW
AU14541/88A 1987-04-10 1988-04-11 3-substituted 1-(2-chlorothiazol-5-yl-methyl)-2-nitroimino- 1,3-diazacycloalkanes Ceased AU604109B2 (en)

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DE3712307 1987-04-10

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US6232309B1 (en) 1989-03-09 2001-05-15 Nihon Bayer Agrochem K.K. Insecticidal heterocyclic compounds
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US5310920A (en) * 1991-12-16 1994-05-10 Mitsui Toatsu Chemicals, Inc. N-vinylimidazolidine derivatives insecticides containing same as an effective ingredient
FR2694752B1 (en) * 1992-08-11 1994-10-14 Roussel Uclaf New imidazole derivatives, their preparation process and their application as pesticides.
DE4232561A1 (en) * 1992-09-29 1994-03-31 Bayer Ag Fighting fish parasites
DE4417742A1 (en) 1994-05-20 1995-11-23 Bayer Ag Non-systemic control of parasites
DE4426753A1 (en) * 1994-07-28 1996-02-01 Bayer Ag Means for controlling plant pests
ZA9610046B (en) * 1995-12-01 1997-07-10 Ciba Geigy Process for preparing 2-chlorothiazole compounds
DE19548872A1 (en) 1995-12-27 1997-07-03 Bayer Ag Synergistic insecticidal mixtures
US6828275B2 (en) 1998-06-23 2004-12-07 Bayer Aktiengesellschaft Synergistic insecticide mixtures
DE19622355A1 (en) 1996-06-04 1997-12-11 Bayer Ag Molded bodies that release agrochemicals
WO1998006710A1 (en) * 1996-08-08 1998-02-19 Novartis Ag Substituted 4-nitroimino-perhydro-1,3,5-oxadiazine derivatives, their use as pesticides and intermediates for their preparation
ID22398A (en) * 1996-12-19 1999-10-07 Novartis Ag THE PROCESS OF THE MAKING OF TIAZOL FRUITS
DE19823396A1 (en) 1998-05-26 1999-12-02 Bayer Ag Synergistic insecticidal mixtures
US6149913A (en) * 1998-11-16 2000-11-21 Rhone-Poulenc Ag Company, Inc. Compositions and methods for controlling insects
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DE19913174A1 (en) 1999-03-24 2000-09-28 Bayer Ag Synergistic insecticidal mixtures
US6156703A (en) * 1999-05-21 2000-12-05 Ijo Products, Llc Method of inhibiting fruit set on fruit producing plants using an aqueous emulsion of eicosenyl eicosenoate and docosenyl eicosenoate
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US8232261B2 (en) 2003-07-18 2012-07-31 Bayer Cropscience Lp Method of minimizing herbicidal injury
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