JP2002515007A - Heterocyclyl-amino- and heterocyclyl-oxy-cycloalkenyl derivatives, their use as pesticides and fungicides - Google Patents

Abstract

(57) Abstract: The present invention provides a compound represented by the formula (a) Wherein, Ar may 4-pyridyl or 4-pyrimidyl optionally substituted in some cases; X is NH, O, S, be SO or SO _2; E is a single bond or alkanediyl; a and b are each 0-3 (not simultaneously 0); R ⁴ is halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy or optionally substituted phenyl; v is 0 It is to 2; U is a single bond, O, S, SO, be imino which may be optionally substituted SO ₂ or; V is a single bond, CO, -CQ-T- or -CT '= N- (Q, T and T' are as defined herein) and R ⁵ is alkyl, alkenyl, alkynyl, optionally substituted aryl or heteroaryl, cyano, NO ₂ , alkyloxyimino Or a silyl group], which is a heterocyclylamino or heterocyclyloxy-cycloalkenyl derivative. The invention also relates to a process for preparing such compounds and to the use of such compounds as pest-control and fungicides.

Description

DETAILED DESCRIPTION OF THE INVENTION Heterocyclyl-amino- and heterocyclyl-oxy-cycloalkenyl derivatives , Insecticides and their use as fungicides   The present invention relates to heterocyclyl-amino- and heterocyclyl-oxy-cycloal Kenyl derivatives, the preparation of these compounds and their use as pesticides and fungicides. It concerns the use of these compounds.   Certain 4-cycloalkoxy-substituted nitrogen-containing heterocyclic compounds can It is already known that it has a tick-killing and bactericidal action (WO 930 0536).   Formula I Novel 4-amino- and 4-alkoxy-substituted nitrogen-containing heterocyclic compounds And salts thereof, preferably acid addition salts.   In the above equation,   R¹Is hydrogen, halogen, (C₁-C_Four) -Alkyl, (C₁-C_Four) -Haloalkyl, (C_Three-C_Five)- Cycloalkyl or (C_Three-C_Five) -Halocycloalkyl;   R^TwoAnd R^ThreeAre the same or different and independently of each other, hydrogen, halo Gen, (C₁-C_Four) -Alkyl, (C₁-C_Four) -Haloalkyl, (C_Three-C₈) -Cycloalkyl, (C_Three -C₈) -Halocycloalkyl, (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Haloalkoxy, (C₁ -C_Four) -Alkoxy- (C₁-C_Four) -Al Kill, (C₁-C_Four) -Haloalkoxy- (C₁-C_Four) -Alkyl, (C₁-C_Four) -Alkoxy- (C₁-C_Four ) -Haloalkyl, (C₁-C_Four) -Haloalkoxy- (C₁-C_Four) -Haloalkyl, (C₁-C_Four) -A Lucylamino, (C₁-C_Four) -Alkylthio, (C₁-C_Four) -Alkylsulfinyl, (C₁-C_Four ) -Alkylsulfonyl, (C₁-C_Four) -Haloalkylthio, (C₁-C_Four) -Haloalkyl sulf Finil, (C₁-C_Four) -Haloalkylsulfonyl, (C₁-C_Four) -Alkylthio- (C₁-C_Four)- Alkyl, (C_Two-C_Four) -Alkenyl, (C_Two-C_Four) -Alkynyl, (C₁-C_Four) -Alkoxycar Bonil, cyano, (C₁-C_Four) -Cyanoalkyl or thiocyano; or   R^TwoAnd R^ThreeTogether with the carbon atom to which they are attached are unsaturated Or a 6-membered homocyclic ring, which is CH 5 if it is a 5-membered ring_TwoAcid instead of May contain an elemental or sulfur atom or the ring may be substituted if it is a 6-membered ring. Should contain one or two nitrogen atoms instead of one or two CH units. And the ring is optionally (C₁-C_Four) -Alkyl, (C₁-C_Four) -Haloal Kill, preferably trifluoromethyl, halogen, (C₁-C_Four) -Alkoxy or (C₁ -C_Four) -Haloalkoxy substituted by one, two or three identical or different groups. May be replaced), or   R^TwoAnd R^ThreeIs, together with the carbon atom to which they are attached, a saturated 5-, 6- Or a 7-membered homocyclic ring, wherein the ring comprises one or two CH_TwoOxygen instead of radicals (Or) may contain sulfur and the ring may optionally be 1, 2 or Is three (C₁-C_Four)-Which may be substituted by an alkyl group);   A is CH or N;   X is NH, oxygen or S (O)_q(Where q = 0, 1 or 2) R;   E is a direct bond or a linear or branched (C₁-C_Four) -Alkanediyl group, Preferably a direct bond;   a and b are the same or different and are each independently of the numbers 0, 1, 2 or 3 (A and b are not simultaneously 0);   R^FourIs halogen, (C₁-C_Four) -Alkyl, (C_Three-C₇) -Cycloalkyl, (C₁-C_Four)-Halo Alkyl, (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Haloalkoxy or optionally An optionally substituted phenyl;   v is 0, 1 or 2;   U is a direct single bond, oxygen, a group S (O)_y(Where y = 0, 1, or 2) Or group NR⁶(Where R⁶Is hydrogen, (C₁-C_Four) -Alkyl or (C₁-C_Four) -Alkoxy );   V is a direct single bond, carbonyl or formula (Where Q is oxygen, sulfur or (C₁-C_Four) -Alkylimino, where T is oxygen, sulfur Or group NR⁶'And T' is (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Alkylthio or Is NR⁶'R⁶"And R⁶'And R⁶"Is the same or different and R⁶Means the above A group with righteousness); and   R^FiveIs an alkyl, alkenyl, alkynyl, optionally substituted Good aryl, optionally substituted heterocyclyl, cyano, Halogen, nitro, alkyloxyimino or group SiR⁷R⁸R⁹(Where R⁷And R⁸ Is (C₁-C_Four) -Alkyl and R⁹Is alkyl, cycloalkyl, aryl or Is an arylalkyl).   And R^FiveAlkyl, alkenyl, alkynyl or alkyl Xyimino group, R⁷, R⁸And R⁹The following features, if appropriate: i. One or more, preferably up to three non-adjacent CHs_TwoThe groups are CO and Or) heteroatom units such as O, S (O)_y(Where y = 0, 1 or 2), NR⁶ '' 'Or SiR⁷'R⁸'(Where R⁶'' 'Is R⁶And has the significance given above for R⁷'And And R⁸'Is R⁷And R⁸Having the meanings indicated above for); ii. 3 to 12 atoms of this group form a ring of up to 12-members; iii. The group is optionally halogen, alkyl, cycloalkyl, aryl , Aryloxy, arylthio, heterocyclyl, heterocyclyloxy, f Terocyclylthio, haloalkyl, arylalkyl, cycloalkylalkyl , Alkoxy, haloalkoxy, alkylthio, cycloalkoxy, alkanoy Ruoxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkyl Rualkanoyloxy, aroyloxy, arylalkanoyloxy, alk Rusulfonyloxy, arylsulfonyloxy, heterocyclylcarbonyl Xy, hydroxyl, cyano and nitro (the cyclics in these substituted Aliphatic, aromatic or heterocyclic ring systems are unsubstituted or up to 3 (halogen, The same or different substitutions, preferably in the case of fluorine and also up to the highest number) Or more than one, preferably 3 Up to (in the case of halogen, up to the highest number) identical or different groups May be replaced by: Has at least one feature of   Preferred compounds of formula I are   R^FourIs halogen, preferably fluorine, chlorine and bromine, (C₁-C_Four) -Alkyl, (C₁- C_Four) -Haloalkyl, (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Haloalkoxy or (C₁-C_Four ) -Alkylthio; and   R^FiveBut (C₁-C₂₀) -Alkyl, (C_Two-C₂₀) -Alkenyl, (C_Two-C₂₀) -Alkynyl, field Optionally substituted aryl, optionally substituted aryl Good heterocyclyl, cyano, halogen, hydroxyl, carboxyl, nitro , (C₁-C₂₀) -Alkyloxyimino or group SiR⁷R⁸R⁹(Where R⁷And R⁸Is (C₁-C_Four ) -Alkyl and R⁹Is (C₁-C₂₀) -Alkyl or optionally substituted Aryl which may be optionally substituted);   And R^FiveAlkyl, alkenyl, alkynyl or alkyl Xyimino group, R⁷, R⁸And R⁹However, where appropriate, the following features: i. One or more, preferably up to three non-adjacent CHs_TwoThe groups are CO and Or) heteroatom units such as O, S (O)_y(Where y = 0, 1 or 2), NR⁶ '' 'Or SiR⁷'R⁸'(Where R⁶'' 'Is R⁶And has the significance given above for R⁷'And And R⁸'Is R⁷And R⁸Having the meanings given above for); ii. 3 to 8 atoms of these groups form a ring of up to 8 members; iii. The group is optionally halogen, (C₁-C₁₂) -Alkyl, (C_Three-C₈) -Cycloa Alkyl, aryl, aryloxy, arylthio, heterocyclyl, heterocyclyl Krilloxy, heterocyclylthio, (C₁-C₁₂) -Haloalkyl, aryl- (C₁-C_Four ) -Alkyl, (C_Three-C₈) -Cycloalkyl- (C₁-C_Four) -Alkyl, (C₁-C₁₂) -Alkoxy , (C₁-C₁₂) -Haloalkoxy, (C₁-C₁₂) -Alkylthio, (C_Three-C₈) -Cycloalkoxy Si, (C₁-C₁₂) -Alkanoyloxy, (C₁-C₁₂) -Haloalkanoyloxy, (C_Three-C₈) -Cycloal Canoyloxy, (C_Three-C₈) -Cycloalkyl- (C₁-C₁₂) -Alkanoyloxy, allo Yloxy, aryl- (C₁-C_Four) -Alkanoyloxy, (C₁-C₁₂) -Alkylsulfo Nyloxy, arylsulfonyloxy, heterocyclylcarbonyloxy, Droxyl, cyano and nitro (the cycloaliphatic, aromatic, The aromatic or heterocyclic ring system is unsubstituted or up to 3 (halogen, preferably Have the same or different substitutions in the case of fluorine and up to the highest number) One or more, preferably up to three (from the system consisting of In the case of halogen, up to the highest number) of identical or different groups And other groups and variables are as described above; And salts thereof, preferably acid addition salts, having at least one feature of You.   More preferred compounds of formula I are   R¹Is hydrogen or fluorine;   R^TwoBut (C₁-C_Four) -Alkyl, cyclopropyl, halocyclopropyl, halo (C₁-C_Two ) -Alkyl, methoxymethyl or cyano;   R^ThreeIs hydrogen, halogen, methyl, ethyl, methoxy, ethoxy, cyano or (C₁-C_Four) -Alkoxycarbonyl; or   R^TwoAnd R^ThreeTogether with the carbon atom to which they are attached, Is an optionally substituted unsaturated 5- or 6-membered ring (when the ring is a 5-membered ring, In the CH_TwoWhich may contain sulfur atoms instead of units), and Is   R^TwoAnd R^ThreeBut, together with the carbon atoms to which they are attached, A 5- or 6-membered ring, wherein the ring is CH_TwoContain sulfur or oxygen atoms instead of units. Can be formed);   A is CH or N;   X is NH or oxygen;   E is a direct bond;   a is the number 1 and b is the number 2;   R^FourIs hydrogen, (C₁-C_Four) -Alkyl, trifluoromethyl or (C₁-C_Four) -Alkoki Is;   And compounds and salts thereof, wherein the other groups and variables are as described above;   In particular,   R¹Is hydrogen;   R^TwoIs methyl, ethyl, propyl, isopropyl, 1-fluoroethyl, tri Fluoromethyl, cyclopropyl or methoxymethyl;   R^ThreeIs halogen, methyl, ethyl, methoxy, ethoxy, cyano or (C₁-C_Four ) -Alkoxycarbonyl; or   R^TwoAnd R^ThreeBut together with the ring system to which they are attached, quinazoline or Quinoline systems, which can be substituted in a carbocyclic moiety by fluorine. Form) or   R^TwoAnd R^ThreeIs, together with the carbon atom to which they are attached, a saturated 6-member Ring (the ring is CH_Two(Can contain oxygen or sulfur atoms in place of groups) And;   v is 0;   U is a direct bond or oxygen;   Compounds wherein V is a direct bond and salts thereof.   Particularly preferred compounds of formula I are   R¹Is hydrogen;   R^TwoIs ethyl, propyl, isopropyl, 1-fluoroethyl, trifluoro Methyl or methoxymethyl;   R^ThreeIs fluorine, chlorine, bromine or methoxy;   Or, when A is nitrogen,   R^TwoAnd R^ThreeTogether with the ring system to which they are attached form the quinazoline system (the The system can be substituted by a fluorine atom), or   R^TwoAnd R^ThreeTogether with the ring system to which they are attached form 5,6,7,8-tetrahydro Form a droquinazoline system;   A is CH or N;   X is NH or oxygen;   E is a direct bond;   a is the number 1 and b is the number 2;   v is 0;   U is a direct bond or oxygen; and   Compounds wherein V is a direct bond and salts thereof.   The most preferred compounds of formula I are   R¹Is hydrogen;   R^TwoIs ethyl or methoxymethyl;   R^ThreeIs fluorine, chlorine, bromine or methoxy; or   If A = N, then R^TwoAnd R^ThreeBut together with the ring system to which they are attached Form a quinazoline or 5,6,7,8-tetrahydroquinazoline system;   R^FiveBut (C₁-C₂₀) -Alkyl, (C_Two-C₂₀) -Alkenyl or (C_Two-C₂₀) -Alkynyl [Three to six carbon atoms of these hydrocarbon groups can form a ring and ( Or) these hydrocarbon radicals are optionally unsubstituted or 3 Up to the same (or, in the case of fluorine, also up to the highest number) identical or different substitutions May be substituted by a phenyl group which can have   A is CH or N;   X is NH or oxygen;   E is a direct bond;   U and V together are a direct bond;   v is 0 and   Compounds and salts thereof, wherein the other groups and variables are as described above;   In particular,   R^TwoIs methoxymethyl and R^ThreeIs methoxy, or   R^TwoIs ethyl and R^ThreeIs chlorine or bromine;   X is NH;   R^FiveBut (C₁-C₂₀) -Alkyl or (C_Two-C₂₀) -Alkenyl (3-6 carbons of this group) The elementary atoms can form a ring and / or the group optionally Unsubstituted or up to 3 (in the case of fluorine, also up to the maximum number) ) Substituted by a phenyl group which can have the same or different substituents May be used); and   Compounds and salts thereof wherein the other groups and variables are as described above.   In the above formula I,   “Halogen” is a fluorine, chlorine, bromine or iodine atom, preferably fluorine, chlorine or Or bromine atoms;   “(C₁-C_Four) -Alkyl "is unbranched or unbranched having 1 to 4 carbon atoms. Or branched hydrocarbon groups such as methyl, ethyl, propyl, isopropyl, Understood as a 1-butyl, 2-butyl, 2-methylpropyl or tertiary butyl group Should be;   “(C₁-C₂₀) -Alkyl "is a group similar to the aforementioned alkyl groups, for example, Pentyl, 2-methylbutyl or 1,1-dimethylpropyl group and hexyl, Heptyl, octyl, 1,1,3,3-tetramethylbutyl, nonyl, 1-decyl, 2-de Understood as a syl, undecyl, dodecyl, pentadecyl or eicosyl group Should be;   “(C₁-C_FourThe term ") -haloalkyl" denotes one or more hydrogen atoms as defined above. "(C substituted by a halogen atom, preferably chlorine or fluorine,₁-C_Four) -A Alkyl "as mentioned in the term" alkyl ", such as trifluoromethyl, 1 -Fluoroethyl, 2,2,2-trifluoroethyl, chloromethyl or fluoro As a romethyl, difluoromethyl or 1,1,2,2-tetrafluoroethyl group Should be understood;   “(C_Three-C_Five) -Cycloalkyl "is preferably cyclopropyl, cyclo To be understood as a butyl or cyclopentyl group;   “(C_Three-C₈) -Cycloalkyl "is preferably cyclopropyl, cycloalkyl Robutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl A tyl group is also understood as a bicyclic system, for example a norbornyl group Should be;   “(C_Three-C₈The term ") -halocycloalkyl" means one or more hydrogen atoms Is replaced by a halogen atom as described above, preferably chlorine or fluorine, "(C_Three -C₈) -Cycloalkyl " Should be understood;   “(C₁-C_FourThe term ") -alkoxy" means that the hydrocarbon radical is "(C₁-C_Four) -Alkyl ” Is to be understood as an alkoxy group having the meaning stated in the word;   “(C₁-C_FourThe term ") -haloalkoxy" means that the halo-hydrocarbon radical is "(C₁-C_Four)-Halo Understood as haloalkoxy groups having the meanings set forth under the term "alkyl" Should be done;   “(C₁-C_Four) -Alkoxy- (C₁-C_Four) -Alkyl "is, for example, 1-methoxy Butyl, 2-methoxyethyl, 2-ethoxyethyl, methoxymethyl or ethyl Understand as toxicoxy group, 3-methoxypropyl group or 4-butoxybutyl group Should be done;   “(C₁-C_FourThe term ") -alkylthio" means that the hydrocarbon group is "(C₁-C_Four) -Alkyl ” It should be understood as an alkylthio group having the meaning stated in the term R;   “(C₁-C_Four) -Alkylthio- (C₁-C_Four) -Alkyl "is, for example, methylthio Methyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-d To be understood as tylthioethyl or 3-methylthiopropyl;   “(C_Two-C_Four) -Alkenyl "is, for example, vinyl, allyl, 2-methyl-2- To be understood as propenyl or 2-butenyl groups;   “(C_Two-C₂₀The term ") -alkenyl" refers to groups similar to the groups mentioned above, e.g. To be understood as a phenyl, 2-decenyl or eicosenyl group;   “(C_Two-C_Four) -Alkynyl "is, for example, ethynyl, propargyl, To be understood as a 2-methyl-2-propyne or 2-butynyl group;   “(C_Two-C₂₀) -Alkynyl "is a group similar to the ones mentioned above, for example 2-pen To be understood as a thynyl or 2-decynyl group;   “(C₁-C_Four) -Alkoxycarbonyl "is, for example, methoxycarbonyl, Ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tertiary butyl To be understood as a oxycarbonyl group;   “(C₁-C1_Two) -Alkoxycarbonyl "is a group similar to the groups described above, e.g. For example, hexyloxycarbonyl, 2-methylhexyloxycarbonyl, decyl Should be understood as an oxycarbonyl or dodecyloxycarbonyl group R;   “Cyano- (C₁-C_FourThe term ") -alkyl" means that the hydrocarbon group is "(C₁-C_Four) -Alkyl "Should be understood as cyanoalkyl groups having the meanings set forth in the term" It is;   “(C₁-C₂₀The term ") -alkylidene" means, for example, exo-methylene, ethylidene , Propylidene, 1-methyl-propylidene, butylidene, octylidene or Should be understood as a desylidene group;   “(C₁-C₂₀The term ") -alkyloxyimino" refers to "(C₁-C₂₀)- Oxiimi etherified by an alkyl group as described in the term "alkyl" Should be understood as   The term "aryl" preferably has 6 to 14, especially 6 to 12, carbon atoms. Preferred homocyclic aromatic groups such as phenyl, naphthyl or biphenylyl, Or phenyl;   The term "heterocyclyl" is defined as a heteroaromatic or heteroaliphatic ring system. It should be understood that a "heteroaromatic ring system" is at least One CH group is replaced by N and / or at least two adjacent CH groups are Aryl groups substituted by S, NH or O, such as thiophene, furan, pyro , Thiazole, oxazole, imidazole, isothiazole, isoxa Zole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4- Triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-tria Zole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo [b] thiophene Benzo [b] furan, indole, benzo [c] thiophene, benzo [c] f Orchid, isoindole, benzoxazole, benzothiazole, benzimida Sol, benzoisoxazole, benzoisothiazole, benzopyrazole, Benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene Benzene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-to Liazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, Quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine , 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, Should be understood as radicals of peptidine, pteridine or 4H-quinolizine; The term "heteroaliphatic ring system" means at least one carbon unit, preferably 3 carbon units. Up to carbon units O, S or NR¹¹(Where R¹¹Is hydrogen, (C₁-C_Four) -Alkyl , (C₁-C_Four) -Alkoxy or aryl)._Three-C₈) -Cyclo Should be understood as an alkyl group;   The term “substituted aryl” refers to halogen, (C₁-C_Four) -Alkyl, (C₁-C_Four)- Haloalkyl, (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Haloalkoxy, (C₁-C_Four) -Arco Kiss- (C₁-C_Four) -Alkyl, (C₁-C_Four) -Alkyl Thio, (C₁-C_Four) -Alkoxy-alkyl, phenyl, phenoxy, halophenoxy , (C₁-C_Four) -Alkylphenoxy, (C₁-C_Four) -Haloalkoxyphenoxy, (C₁-C_Four)- Haloalkylphenoxy, phenylthio, heterocyclyl, heterocyclylthio Or one or more, preferably from a system consisting of heterocyclyloxy, preferably Has up to 3 (up to the highest number in the case of fluorine) identical or different groups Should be understood as an aryl group which can be   The term “substituted heterocyclyl” refers to the term “substituted aryl” 1 or more, preferably up to 3 (fluorine) In the case of elementary and also up to the highest number) of identical or different groups Should be understood as a possible heteroaromatic or heteroaliphatic ring system;   Optionally substituted "cycloaliphatic, aromatic and heterocyclic The formula group "is, for example, one or more, preferably up to three (in the case of fluorine, Or up to the highest number) of "substituted aryl" Aryloxy, arylthio, heterocyclyl which can have different substitutions Ryloxy, heterocyclylthio, aroyl, aroyloxy, cycloalkyl Or as a group such as cycloalkanoyl;   “Aryl- (C₁-C_Four) -Alkyl "is substituted by an aryl group Is “(C₁-C_Four) -Alkyl "should be understood as the alkyl group mentioned in the term. It is;   The term "aryloxy" refers to, for example, phenoxy or 1- or 2-naphthyl. Should be understood as a ruoxy group;   The term "arylthio" refers to, for example, phenylthio or 1- or To be understood as a 2-naphthylthio group;   The term “heterocyclyloxy” or “cyclocyclylthio” refers to oxygen or Or one of the above-mentioned heterocyclic groups linked via a sulfur atom. is there.   Substituents that various aliphatic, aromatic or heterocyclic ring systems may have are, for example, Halogen, (C₁-C_Four) -Alkyl, trimethylsilyl, (C₁-C_Four) -Haloalkyl, (C₁- C_Four) -Alkoxy, (C₁-C_Four) -Haloalkoxy, (C₁-C_Four) -Alkoxy- (C₁-C_Four) -Al Kill, (C₁-C_Four) -Alkylthio, alkylsulfinyl, alkylsulfonyl, Phenyl, phenoxy, halophenoxy, (C₁-C_Four) -Alkylphenoxy, (C₁-C_Four)- Alkoxyphenoxy, (C₁-C_Four) -Haloalkoxyphenoxy, (C₁-C_Four) -Haloal Kilphenoxy, phenylthio, heterocyclyl, heterocyclylthio or f Terocyclyloxy [one or more in an alkyl group and a group derived therefrom; Represents two or more (in the case of fluorine or up to the maximum) hydrogen atoms Optionally substituted by chlorine, or fluorine].   further,   “R^FiveAlkyl, alkenyl, alkynyl or alkyloxy mentioned for Imino group, R⁷, R⁸And R⁹The following features, if appropriate: i. One or more, preferably up to three non-adjacent CHs_TwoThe groups are CO and Or) heteroatom units such as O, S (O)_y(Where y = 0, 1 or 2), NR⁶ '' 'Or SiR⁷'R⁸'(Where R⁶'' 'Is R⁶And has the significance given above for R⁷'And And R⁸'Is R⁷And R⁸Having the meanings indicated above for); ii. 3 to 12 atoms of these groups form a ring of up to 12-members; iii. The group is optionally halogen, alkyl, cycloalkyl, aryl , Aryloxy, arylthio, heterocyclyl, heterocyclyloxy, f Terocyclylthio, haloalkyl, arylalkyl, cycloalkylalkyl , Alkoxy, haloalkoxy, alkylthio, cycloalkoxy, alkanoy Ruoxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkyl Rualkanoyloxy, aroyloxy, arylalkanoyloxy, alk Rusulfonyloxy, arylsulfonyloxy, heterocyclylcarbonyl Xy, hydroxyl, cyano and nitro (the cyclic lipids in these listed substitutions) Aliphatic, aromatic or heterocyclic ring systems are unsubstituted or up to 3 (halogen, Preferably in the case of fluorine, and also up to the highest number) of the same or different One or more, preferably three, from the system consisting of (Up to the highest number in the case of halogens) May be replaced by: Having at least one characteristic of an alkoxyalkyl A methoxymethyl, methoxyethyl or ethoxyethyl group; or Alkoxy-alkoxy-alkyl groups such as methoxy- or ethoxy-ethoxy Ethyl; or alkylthioalkyl, such as methyl- or ethylthio A tyl group; or an alkylsulfinylalkyl group, for example methyl- or ethyl A sulfinylethyl group; or an alkylsulfonyl-alkyl group such as methyl- Or ethylsulfonylethyl group; or alkyl-dialkylsilyl-alkyl A group such as a trimethylsilylmethyl or ethyldimethylsilylethyl group; Is an alkyl-cycloalkyl group such as 4-methyl-cyclohexyl, 3-ethyl- Cyclopentyl or 4-tert-butyl-cyclo A hexyl group; or a cycloalkyl-alkyl group, such as cyclohexylmethyl , Cyclohexylethyl, cyclohexylpropyl, cyclohexylbutyl or Is a 1-cyclohexyl-1-methylethyl group or an aryl-alkyl group, for example, Benzyl, 2-phenylethyl, 1-phenylethyl or 1-methyl-1-phenyl Ethyl group, 3-phenylpropyl or 4-phenylbutyl group, 2-methyl-2-phenyl Enyl-ethyl group or 1-methyl or 2-methylnaphthyl group; Kurylalkyl groups such as thienylmethyl, pyridylmethyl, furfuryl, tet Lahydrofurfuryl, tetrahydropyranylmethyl or 1,3-dioxolan-2- An ylethyl group; or an aryloxyalkyl group such as phenoxymethyl or Is a naphthoxymethyl group; or "(C_Three-C₈) -Cycloalkyl "above Monocyclic, such as norbornyl or bicyclo [2.2.2] octane Cycloalkyls which are condensed such as bicyclic or decahydronaphthyl groups Haloalkyl derivatives of the corresponding groups, such as haloalkyl , Haloalkoxyalkyl, alkoxyhaloalkyl, haloalkyl-cyclo Includes alkyl or halocycloalkyl groups.   The above remarks apply accordingly to analogs and groups derived therefrom. It is.   The above description refers to groups where the specific number of carbon atoms is not stated accordingly. And analogs or groups derived therefrom.   The present invention relates to compounds of formula I in the form of a free base or an acid addition salt. . Acids that can be used for salt formation include inorganic acids such as hydrochloric acid, hydrobromic acid , Nitric acid, sulfuric acid or phosphoric acid, or organic acids such as formic acid, acetic acid, propionic acid, oxalic acid Acid, fumaric acid, adipic acid, stearic acid, With oleic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid is there.   Compounds of formula I often have one or more chirality elements. So Hence, racemates or diastereomers can exist. The present invention It relates to pure isomers and mixtures thereof. Diastereomeric mixture Can be obtained by conventional methods, for example by selective crystallization from a suitable solvent or by The components can be separated by chromatography. Racemic is a conventional Depending on the method, for example, salt formation with optically active acids, separation of diastereomeric salts And separation of enantiomers by release of pure enantiomers by base can do.   Further, the present invention provides a compound of formula II (Where A, R¹, R^TwoAnd R^ThreeHas the meanings described in formula I and L is an example For example, halogen, alkylthio, alkanesulfonyloxy or arylsulfo Leaving groups such as niloxy, alkylsulfonyl or arylsulfonyl. Of formula III (Where X, E, a, b, v, U, V, R^FourAnd R^FiveIs the meaning described in formula I With a nucleophile) and R^ThreeIs appropriate if is hydrogen When is it obtained in this way or otherwise obtained The compound of formula I is halogenated at the 5-position of the heterocyclic group, preferably a salt Bromination or bromination or R in the side chain^FiveOf formula I comprising further derivatization of The present invention relates to a method for producing the compound of   The above-mentioned substitution reactions are known in principle. The leaving group L is Can be varied and, for example, halogen atoms, such as fluorine, chlorine, bromine, etc. Or iodine, alkylthio, such as methyl- or ethylthio, or alkanth Ruphonyloxy, for example methane-, trifluoromethane- or ethanesulfonyl Oxy or arylsulfonyloxy, such as benzenesulfonyloxy or Or toluenesulfonyloxy, or alkylsulfonyl, such as methyl- or Or ethyl-sulfonyl, or arylsulfonyl, such as phenyl- or It can be ruene-sulfonyl.   The reaction described above is advantageously effected in the presence of a base and, where appropriate, inactive. Organic solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, Methyl sulfoxide, N-methylpyrrolidin-2-one, dioxane, tetrahydride Lofran, 4-methyl-2-pentanone, methanol, ethanol, butanol, Ethylene glycol, ethylene glycol dimethyl ether, toluene, chloro It is carried out in benzene or xylene in a temperature range from 20 to 150 ° C. The solution described above Mixtures of agents can also be used. Suitable bases include, for example, alkali metals. Or alkaline earth metal carbonates, bicarbonates, amides or hydrides, such as carbonic acid Sodium, sodium bicarbonate, potassium carbonate, sodium amide or hydrogenated Sodium or organolithium compounds such as n-butyllithium.   A suitable base when X is oxygen is, for example, an alkali metal or Are alkaline earth metal carbonates, bicarbonates, amides or hydrides, such as sodium carbonate Thorium, sodium bicarbonate, potassium carbonate, sodium amide or hydrogenated A suitable base when thorium and X is NH is, for example, alkali Metal or alkaline earth metal carbonates, bicarbonates, hydroxides, amides or hydrogen Compounds such as sodium carbonate, sodium bicarbonate, potassium carbonate, sodium hydroxide Sodium, sodium amide or sodium hydride or an organic base such as trie Tylamine or pyridine. Secondary equivalents of amines of formula III also assist It can be used as a base.   The starting compounds of the formula II are known or these compounds are synthesized according to known methods. It can be manufactured by various methods. For example, see the description below.   Quinoline: Org. Synth., Coll. Vol. 3,272 (1955).   1,5-Naphthyridine: J. Amer. Chem. Soc. 68, 1317 (1946) and English                     National patent 1147760.   1,6-Naphthyridine: J. Chem. Soc. 1960, 1790.   1,7-Naphthyridine: J. Org. Chem. 19, 2008 (1954).   1,8-Naphthyridine: Synthesis 1974,809.   Pyridopyrimidine: EP-A-414 386.   Pteridine: J. Chem. Soc. 1951,474.   The starting material used when A is a nitrogen atom is an acetoacetic ester derivative Which is converted to the halopyrimidine via the corresponding hydroxypyrimidine Is done.   In addition, the starting compound of formula II can be prepared from the malonic ester derivative in a manner similar to that known from the art. Can be obtained by various methods.  R^ThreeOf the formula II wherein is a halogen is obtained by halogenation according to known methods be able to.   The nucleophile of formula III required as a starting material, when X is oxygen, By known methods, for example, the carbonyl group can be converted to a suitable reducing agent, for example, By reduction with chloride or, in the case of aldehydes or ketones, also hydrogen And reduction with a hydrogenation catalyst, Can be manufactured. For particularly preferred cis-cyclohexyloxy derivatives In order to produce the precursor cis-cyclohexanol, Catalytic hydrogenation of substituted phenols or composites with very bulky substitutions Hydrides, such as L-selectride (L- Are particularly suitable.   When X is NH, the nucleophile of formula III required as a starting material is By known methods, for example, a suitable reducing agent, such as a complex metal hydride or hydrogen Reduction of oximes or nitriles with hydrogen in the presence of added catalysts, aldehydes Reductive amination of metal or ketone or Leuckaer-Wallach reaction or alkyl halide It can be produced by Gabriel reaction of ride or tosylate. Especially good Cyclohexyl, a Precursor for Preferred Cyclohexylamino Derivatives To produce amines, ammonium salts and sodium cyanoborohydride According to or ammonia and nickel, ruthenium, rhodium or palladium Suitably substituted cyclohexano by hydrogen in the presence of a metal catalyst such as Reductive amination of cis-amines is particularly suitable, and the desired cis-amine is The content is particularly high. Another method is to hydrogenate amines in the presence of a hydrogenation catalyst. It is addition.   In order to prepare a precursor for a particularly preferred cyclohexanyl derivative The following reactions are particularly suitable: 1) Alkyl, alkenyl or aryl derivatives (a = 1, b = 2, U and V = Direct binding) 2) alkyl, alkenyl or aryl derivatives (a = 1, 2 or 3, b = 1 , 2 or 3, U and V = direct bond) 3) Cyclohex-3-enyl-amino and -alkoxy derivativesPreparation of 1-methoxy-1,4-cyclohexadiene or cyclohex-3-enone:   J. Chem. Soc. Perkin Trans 1, 7 (1983); Org. Chem. 29, 2351 (1964); J . Org. Chem. 41, 531 (1976).   It has good plant tolerance and favorable toxicity to warm-blooded animals, Sexual compounds control animal pests, especially insects, arachnids, parasites and mollusks Very particularly preferably for agriculture, animal husbandry, forestry, protection of stored materials and Suitable for controlling insects and arachnids found in the hygiene field. These compounds are useful in species that are normally sensitive and resistant and in all individual developmental stages. Active on the floor. The above mentioned pests include:   From the order Acarina, for example, Acarus siro, Argas spp., Ornithodoros s pp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma s pp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcop tes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranych us spp., Eotertanychus spp., Oligonychus spp. and Eutetranychus spp.   From the order of the isopod (Isopoda), for example, Oniscus asselus, Armadium vulgar and Por cellio scaber.   From the order of the Diplopoda, for example, Blaniulus guttulatus.   From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.   From the order of the joint (Symphyla), for example, Scutigerella immaculata.   From Thysanura, for example, Lepisma saccharina.   From the order of the Collembola, for example, Onychiurus armatus.   From the order Orthoptera, for example, Blattaorientalis, Periplaneta american a, Leucophaea madeirae, Blatella germanica, Achetadomesticus, Gryllotalp a spp., Locusta migratoria migratorioides, Melanoplus differentialis and And Schistocerca gregaria.   From the order of the Isoptera, for example, Reticulitermes spp.   From the louse (Anoplura), for example, Phylloera vastatrix, Pemphigus spp., P ediculus humanus corporis, Haematopinus spp. and Linognathus spp.   From the order of the pilocene (Mallophaga), for example, Trichodectes spp. And Damalina sp p.   From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.   From the suborder Heteroptera, for example, Eurygaster spp., Dysdercus intermed ius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma  spp.   From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Crypto myzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopteru s arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosip hum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lec anium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens , Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. And Psylla  spp.   From the butterfly moth Lepidoptera, for example, Pectinophora gossypiella, Bupalu s piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta  padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorr hoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, S podopteraspp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo  spp., Pylausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cac oecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambigue lla, Homona magnanima and Tortrix viridana.   From the order Coleopera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes baju lus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Di abrotica spp., Psylloides chrysocephala, Epilachan varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otior rhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hype ra postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Atriotes spp., Conoderus s pp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zea landica.   From Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius  spp., Monomorium pharaonis and Cespa spp.   From the order of the Diptera, for example, Aedes spp., Anopheles spp., Cules spp., D rosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocepha la, Lucilia spp., Chrysomyia spp., Cuterbra spp., Gastrophilus spp., Hypo bosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., T annia spp., Bibiohortulanus, Oscinella frit, Phorbia spp., Pegomyia hyos cyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.   From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophy llus spp.   From the order Arachnida, for example, Scorpio maurus and Latrodectus mactans .   From the parasite net (Helminths), for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostro ngulus, Ancylostoma, Ascaris and Heterakis and Fasciola and phytotoxicity Nematodes, for example, Meloidogyne, Heterodera, Ditylenchus, Aphelenchoides, Rado Nematodes from the genera pholus, Globodera, Pratylenchus, Longidorus and Xiphinema.   From the gastropod (Gastropoda), for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and On comelania spp.   From the Bivalva web, for example, Dreissena spp.   Plant parasitic nematodes that can be controlled by the present invention include, for example, root-parasitic soil. Nematodes, such as the genus Meloidogyne (root-knot nematodes, such as Meloidogyne incognita, Meloid ogyne hapla and Meloidogyne javanica), Heterodera and Globodera Strike-forming nematodes, such as Globodera restochiensis, Globodera pallida and Het eroderatrifolii), and genus Radopholus, for example, Radopholus similis, Pratylen chus, such as Pratylenchus neglectus, Pratylenchus penetrans and Pratyl enchus curvitatus, genus Tylenchulus, such as Tylenchulus semipenetrans, Tylen genus chorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus clayt oni, genus Rotylenchus, such as genus Rotylenchus robustus, Haliocotylenchus Haliocotylenchus multicinctus, genus Belonoaimus, for example, Belonoaimus longic audatus, genus Longidorus, such as genus Longidorus elongatus, trichodorus, such as T richodorus primitivus and Xiphinema genus, such as nematodes of Xiphinema index Include.   Genus Ditylenchus (stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor), genus Aphelenchoides (leaf nematodes such as Aphelenchoides ritzemabosi) and nematodes of the genus Anguina (flower nematodes such as Anguina tritici) It can be controlled with a compound according to Ming.   The present invention also relates to a composition comprising a compound of the formula I in addition to suitable formulation auxiliaries, In particular, it relates to insecticidal and acaricidal compositions.   The compositions according to the invention generally comprise the active compounds of the formula I in the range from 1 to 95% by weight. Have.   The composition depends on the biological and / or chemical-physical parameters. It can be formulated in various ways as defined. Therefore, appropriate prescription Performance is hydratable powder (WP), emulsion stock solution (EC), aqueous solution (SL), emulsion, spray solution , Oily or aqueous dispersion (SC), suspoemulsion (SE), dust (DP), seed dressing Granules in the form of artificial, micro, spray, absorbed and adsorbed granules, water-dispersible granules (WG), ULV formulation, microcapsules, wax or poison.   These individual types of formulations are known in principle and are described, for example, in the following documents: It is listed. Volume 7, C. Hauser Verlag Munich, 4th Edition 1986; van Falkenberg, “Pe sticides Formulations ", Marcel Dekker N.Y., 2nd Edition 1972-73; K. Mart ens, “Spray Drying Handbook”, 3rd Edition 1979, G. Goodwin Ltd., London .   The necessary formulation aids such as inert substances, surfactants, solvents and other additives are Are also known and described, for example, in the following documents:   Watkins, “Handbook of Insecticide Dust Diluents and Carriers” 2nd Edition, Darland Books, Caldwell N.J .; H.v. Olphen, “Introduction to  Clay Colloid Chemistry ”, 2nd Edition, J. Wiley & Sons, N.Y .; Marschen, “Solvents Guide”, 2nd Edition, Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J .; Si sley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Technologie (Chemical Technology) ", Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.   Also in combination with other pesticidally active substances, fertilizers and / or growth regulators Or based on these formulations, for example in the form of ready-to-use formulations or Can be manufactured as a tank mixture. Hydrating powders are evenly dispersed in water It can be added to active compounds and diluents or inert substances. Wetting agents, such as polyoxyethylated alkylphenols, polyoxyethylene Alkylated fatty alcohol or alkyl- or alkylphenol-sulfonate And dispersants such as sodium ligninsulfonate or 2,2'-dinaphthyl meta Contains sodium 6,6'-disulfonate. One or more emulsion stocks Active compound in an organic solvent such as butanol, Rohexanone, dimethylformamide or xylene or otherwise Produced by dissolving in high boiling aromatic solvents or hydrocarbons. use Emulsifiers that can be used include, for example, calcium alkylaryl sulfonates, For example, dodecylbenzene Calcium sulfonate or non-ionic emulsifiers such as fatty acid polyglycol es Ter, alkylaryl polyglycol ether, fatty alcohol polyglycol Ether, propylene oxide / ethylene oxide condensation product, alkyl polyether Sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc. Or polyoxyethylene sorbitol ester.   Dusts form the active compound in finely divided solid substances, for example talc or naturally occurring substances. With clay, such as kaolin, bentonite, pyrophyllite or diatomaceous earth Obtained by crushing. Granules are granular inert which adsorb active compounds By spraying on the substance or by applying the active compound stock solution to an adhesive, e.g. With vinyl alcohol, sodium polyacrylate or otherwise mineral oil. Manufactured by applying to the surface of sand, kaolinite or particulate inert material. Can be Suitable active compounds can also be mixed with fertilizers if necessary Thus, it can be granulated in a manner conventional for the production of fertilizer granules.   In wettable powders, the active compound concentration is, for example, about 10-90% by weight. The remainder, based on 100% by weight, consists of conventional ingredients. In the emulsion stock solution, The concentration of active compound is about 5-80% by weight. Dust-like formulations are usually active compounds The spray solution contains 5 to 20% by weight and the spray solution contains about 2 to 20% by weight of active compound. In granules, the active compound content may depend, in part, on the active compound in liquid or solid form. Which form is present and which granulation aids, extenders, etc. Depends on   In addition, the formulation of the active compounds mentioned above may, where appropriate, Contains agents, wetting agents, dispersants, emulsifiers, penetrants, solvents, extenders or carrier substances .   For use, commercially available stock solutions should be prepared in a suitable In the case of hydratable powders, emulsion stock solutions and dispersions, use a conventional method. In some cases, the microgranules are diluted with water. Powdery and granular Formulations and spraying solutions are usually not diluted with additional inert materials prior to use.   The required amount of application varies depending on external conditions such as temperature and humidity. that is Within a wide range, for example 0.0005 to 10.0 kg / ha or more of active substance, Preferably it can vary between 0.001 and 5 kg / ha.   Commercially available formulations and use forms made from these formulations In one embodiment, the active compounds according to the invention are other active compounds, such as insecticides, attractants. With attractants, sterilants, acaricides, nematicides, fungicides, growth-regulators or herbicides It can be present as a mixture.   Pest control agents include, for example, phosphate esters, carbamates, carboxylate esters, e.g. Lumamidine, tin compounds, substances produced by microorganisms and the like. mixture Preferred partners in are as follows. 1. From the group of phosphorus compounds,   Acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, bromine Mophos, bromophos-ethyl, chlorfenvinphos, chlormefos, chlorpi Liphos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S -Methylsulfone, dialiphos, diazinone, dichlorvos, dicrotophos, 0.0 -1,2,2,2-tetrachloroethyl-phosphorothioate (SD 208 304), dimethoate G, disulfoton, EPN, ethion, etoprophos, etrimphos, famful , Fenamiphos, phenytrithione, fensulhotion, fenthion, e No Phos, formothion, heptenophos, inzophos, isothioate, isoxati On, malathion, methacrifos, methamidophos, methidathion, salicion, Mevinphos, monocrotophos, naled, ometoate, oxydemeton-methyl , Parathion, parathion-methyl, fentoate, holate, hosalon, ho Suholane, Hosmet, Phosphamidone, Foxime, Pirimiphos, Pirimiphos- Ethyl, pirimiphos-methyl, propenophos, propaphos, proethamphos, Prothiophos, pyraclophos, pyridapentione, quinalphos, sulprophos, Temefos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Lichlorfon, bamidione; 2. From the carbamate group,   Aldicarb, 2-sec-butylphenylmethyl carbamate (BPMC), carbali , Carbofuran, carbosulfan, cloetocarb, benfracarb, d Thiophenecarb, furatiocarb, isoprocarb, methomyl, 5-methyl-m -Cumenylbutyryl (methyl) carbamate, oxamyl, pirimicarb, pro Poxal, thiodicarb, thiophanox, 4,6,9-triaza-4-benzyl-6,1 Ethyl 0-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate (OK 135) 1,1-methylthio (ethylideneamino) -N-methyl-N- (morpholinothio) cal Bamate (UC 51717); 3. From the group of carboxylic esters,   Aletrin, alphamethrin, (E)-(1R) -cis, 2,2-dimethyl-3- (2-O Oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate 5-benzyl-3- Furylmethyl, bioalethrin, bioalethrin ((S) -cyclopentyl isomer) , Bioresmethrin, bifenay G, (1RS) -trans-3- (4-tert-butylphenyl) -2,2-dimethylcyclopropa N-carboxylate (RS) -1-cyano-1- (6-phenoxy-2-pyridyl) methyl (NCI 85 193), cycloprothrin, cyhalothrin, cyttrin, cypermethrin, cyfe Notrin, Deltamethrin, Empentrin, Esfenvalerate, Fenfu Rutrin, fenpropatrin, fenvalerate, flucitrinate, flume Trin, fluvalinate (D isomer), permethrin, pheothrin ((R) isomer) , D-Praletrin, pyrethrins (naturally occurring products), resmethrin, Tefluthrin, tetramethrin, tralomethrin; 4. From the amidine group,   Amitraz, chlordimeform; 5. From the group of tin compounds,   Cyhexatin, fenbutatin oxide; 6. Other   Abamectin, Bacillus thuringien-sis, Sultap, binapacryl, bromopropylate, buprofezin, camfe Chlor, cartap, chlorobenzylate, chlorfluazuron, 2- (4-chloro Rophenyl) -4,5-diphenylthiophene (UBI-T 930), chlorfentezine, 2-naphthylmethyl clopropanecarboxylate (Ro 12-0470), cyromazine, ethyl N- (3,5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propyloxy) Nyl) carbamoyl) -2-chlorobenzocarboxymate, DDT, dicophor, N -(N- (3,5-dichloro-4- (1,1,2,2-tetrafluoroethoxy) phenylamino) Carbonyl) -2,6-difluorobenzamide (XRD 473), diflubenzuron, N- (2 , 3-Dihydro-3-methyl-1,3-thiazole Ru-2-ylidene) -2,4-xylidine, dinobutone, dinocap, endosulfan , Etofenprox, (4-ethoxyphenyl) (dimethyl) (3- (3-phenoxy) (Ciphenyl) propyl) silane, (4-ethoxyphenyl) (3- (4-fluoro-3- Phenoxyphenyl) propyl) dimethylsilane, phenoxycarb, 2-fluoro B-5- (4- (4-ethoxyphenyl) -4-methyl-1-pentyl) diphenylate (MTI 800), granulomatosis and pleiotropic virus, fenthiocarb, flubenz Imine, flucycloxuron, flufenoxuron, gamma-HCH, hexiti Azox, hydramethylnon (AC 217300), ivermectin, 2-nitromethyl -4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothio Azole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-silcarbamal Dehyde (WL 108477), propargite, teflubenzuron, tetradihon, tet Rasul, thiocyclam, trihumulone, imidacloprid.   The active compound content of the use forms prepared from commercially available formulations is 0.00000001 to 95% by weight, preferably 0.00001 to 1% by weight. Wear.   These formulations are used in a customary manner appropriate for these forms of use.   The active compounds according to the invention can also be used in veterinary medicine and in animal husbandry. It is also suitable for controlling internal and ectoparasites.   The active compounds according to the invention can be prepared in a known manner, for example in tablets, capsules, drinking water or the like. Oral use in the form of granules or granules, such as dipping, spraying, pouring (pour Transdermal use in the form of dusts and powders) and Used by parenteral use in the form of cum Is done.   Thus, the novel compounds of the formula I according to the invention can also be used for livestock breeding (eg cattle, sheep) , Pigs and poultry, such as chickens or goose). it can. In a preferred embodiment of the invention, the novel compounds are If appropriate, with appropriate formula (see above) and, if appropriate, with drinking water or feed Orally administered to animals. The compound is excreted in the feces in an effective way, Insect development in animal droppings can be very easily prevented in this way. You. Certain appropriate dosages and formulas will depend, inter alia, on the type and developmental stage Also depends on the degree of intrusion and is easily determined and specified by conventional methods can do. In the case of cattle, the new compound is, for example, It can be used in an amount of 0.01 to 1 mg.   The compounds of the formula I according to the invention are also distinguished by a pronounced bactericidal action. Pathogens that have already penetrated the plant tissue can advantageously be controlled therapeutically. This It can no longer be effectively controlled with other conventional fungicides after the infection has taken place. Particularly important and advantageous in the case of fungal diseases. Of the compound of the invention The spectrum of action is determined by various economically important plant pathogens, such as Plasmopara vit icola, Erysiphe graminis, Phytophthora infestaus, Pyricularia oryzae, Py renophora teres, Leptosphaera notorum, Pellicularia sasakii and Puccini a recondita.   Furthermore, the compounds according to the invention can also be used in the industrial field, for example in wood preservatives, paints. Preservatives or drilling oils in cooling lubricants and for metalworking Also suitable for use as a preservative in cutting oils.   The active compounds according to the invention can be used on their own or in other fungicides known from the literature. In combination with the agent, it can be used in commercially available formulations.   For example, known from the literature and combined with the compounds of the formula I according to the invention The following products can be listed as fungicides that can be used:   Aldimorph, Fundprim, Anilazine, BAS 480F, BAS 450F, Benalax , Benodanil, benomyl, binapacryl, bitertanol, bromconazole , Butiobate, captaphor, captan, carbendazim, carboxin, CGA 173506, ciprofram, diclofluanid, diclomedin, diclobutrazol , Dietofencarb, difenconazole (CGA 169374), difluconazole, Dimethyimol, dimethomorph, diniconazole, dinocap, dithianon, dode Morph, dozine, edifenphos, ethylmol, etridiazole, fenarimo Fenfenram, fenpiclonil, fenpropidine, fenpropimorph , Fentin acetate, fentin hydroxide, ferimzone (TF 164), Luazinam, fluorbenzimine, fluquinconazole, fluoridimide, fluci Lazole, Flutolanil, Flutriafol, Folpet, Josetyl-aluminium Fluberdazole, flusulfamide (MT-F 651), flalaxil, fluconazo , Flumesyl Crocs, Guazatine, Hexaconazole, ICI A5504, Mazaril, imibenconazole, iprobenfos, iprodione, isoprothio Orchid, KNF 317, copper compounds such as copper oxychloride, oxine-Cu and copper oxide, Ncozeb, maneb, mepanipyrim (KIF 3535), metconazole, mepronil, meconil Taraxyl, metasulfocarb, metofloxam, MON 24000, microbutanil , Nabam, Nitrothalidopropyl, Nuarimol, Ophra , Oxadixyl, Oxycarboxin, Penconazole, Pencyclone, PP  969, probenazole, propineb, prochloraz, procymidone, propamoca Rubu, propiconazole, prothiocarb, pyracarbolide, pyrazophos, pyri Phenox, Pyroquilon, Ravenzazole, RH 7592, Sulfur, Tebuconazole , TF 167, thiabendazole, thithiophene, thiophanate-methyl, thiram , Tolclofos-methyl, tolylfluanid, triadimefon, triadimenow , Tricyclazole, tridemorph, triflumizole, triforine, valida Mycin, vinclozolin, XRD 563, zineb, sodium dodecyl sulfonate , Sodium dodecyl sulfate, C13 / C15-alcohol ether-sodium sulfonate Sodium, cetostearyl phosphate, dioctyl sodium sulfosuccinate Sodium, sodium isopropyl-naphthalenesulfonate, methylenebisnaphthale Sodium-sulfonate, cetyl-trimethylammonium chloride, long chain Primary, secondary or tertiary amine salts, alkyl-propylene amines, lauryl Pyrimidinium bromide, ethoxylated quaternized fatty amine, alkyl-dim Tyl-benzylammonium chloride and 1-hydroxyethyl-2-alkyl -Imidazoline.   The combination partners mentioned above are known active compounds, most of which Is Ch. R. Worthing, S.M. B. Walker, The Pesticide Manual, 7th Edition (198 3), described in the British Crop Protection Council. Commercially available The active compound content of the use forms prepared from the formulations may be varied within wide ranges. And the concentration of active compound in use forms may be from 0.0001 to 95% by weight of active compound. %, Preferably between 0.0001 and 1% by weight. Prescription depends on usage form In a suitable conventional way used.   The following examples are provided to illustrate the present invention, and the present invention provides It is not limited by these examples. A. Examples of prescription a) Powders consist of 10 parts by weight of active compound and 90 parts by weight of talc as inert substance. And milling the mixture in a hammer mill. b) A hydratable powder that can be easily dispersed in water contains 25 parts by weight of active compound, Parts by weight of kaolin-containing quartz, ligninsul as wetting agent and dispersant 10 parts by weight of potassium phonate and 1 part by weight of sodium oleoyl methyl tauride It is obtained by mixing and grinding the mixture in a pin disc mill. c) Dispersion stock solution that can be easily dispersed in water contains 40 parts by weight of active compound 7 parts by weight of acid half ester, 2 parts by weight of ligninsulfonic acid sodium salt and 51 parts of water Parts and mix the mixture in a grinding bead mill to a fineness of less than 5 microns. Manufactured by crushing. d) Emulsion stock solution contains 15 parts by weight of active compound and 75 parts by weight of cyclohexane as solvent. Oxyethylated nonylphenol as an emulsifier and ethylene oxide unit 10 It can be manufactured from parts by weight. e) Granules are from 2 to 15 parts by weight of the active compound and an inert particulate carrier such as Ataple Manufactured from gite, pumice grains and / or quartz sand. Advantageously, A suspension of the hydratable powder from Example b) having a solids content of 30% is used and Is sprayed onto the surface of the attapulgite grains and the material is dried and mixed evenly. Combine. The weight of the hydratable powder is about 5% of the final granules and of the inert carrier material Weight is about 95% of final granule It is. B. Biological examples Insecticidal and acaricidal action Example 1: Action on brown planthopper   Young rice plants (Oryza sativa), with a concentration of 250 ppm (based on active compound) After soaking in an aqueous dilution of the wettable powder stock solution and draining, the plants were treated with 9 L4 larval stages. Infiltrate the brown planthopper Nilaparvata lugens. After putting them in the test basket, Were observed at 28 ° C. and high atmospheric humidity for 3 days and the mortality of the test animals was determined.   100% mortality of test animals at 250 ppm with compounds according to Examples B and C Indicated. Example 2: Action on Diabrotica undecimpunctata   Larvae of corn cricket beetle (Diabrotica undecimpunctata) from the south (L3 ) In each case with a wettable powder at a concentration of 250 ppm based on the active compound Place on a filter paper disc impregnated with 1 ml of acetone dilution. Remove acetone by evaporation After that, the disc is sealed and kept at 28 ° C. for 3 days and then larval death Mortality was measured. Using the compounds according to Examples B and C, a mortality of 100% Was found. Example 3: Effect of American red stink bug on eggs   Eggs (2 days old) of American red stink bug (Oncopeltus fasciatus) Filter paper discs containing in each case 250 ppm of the specific active compound. Treat with 1 ml of the aqueous formulation. After drying, remove the filter paper disc at room temperature and And in a Petri dish with the highest atmospheric humidity. After 7 days, the ovicidal effect was measured . A 100% ovicidal effect (egg mortality) was observed using the compounds of Examples B and C. Was issued. Example 4: Action on black bean aphids   Broad bean plants infested with black bean aphids (Aphis fabae, growing population) vigorously (Vicia faba) until the formulation starts to drip and drop, Spray an aqueous formulation containing 0 ppm. After growing the plants in the greenhouse for 3 days, The mortality of the viper was examined. Using the compounds of Examples A, B, C and D 100% mortality was found. Example 5: Action on common spider mites   Bean plants (Tetranychus urticae, growing population) that invaded vigorously Phaseolus vulgaris ssp. vulgaris var. nanus) Spray with an aqueous formulation containing 250 ppm of the particular active compound until complete. Plants After growing in a greenhouse for 7 days, spider mites (growing populations) were examined for mortality. Example A, 100% mortality was found using compounds B, C and D. Example 6: Effect of fruit tree on spider mites   Apples vigorously invaded the fruit tree spider mite (Panonychus ulmi, growing population) Specific activation of the plant (Malus domestica) until the formulation begins to drip Spray an aqueous formulation containing 250 ppm of the compound. Plants were grown in the greenhouse for 9 days Later, the mortality of spider mites (growing populations) on the fruit trees was examined. Examples A, B, C and Using compound D, a mortality rate of 100% was found. Example 7: Citrus mealybug   Bald citrus mealybug (Planococcus citri, second stage larva) To the bean plant (Phaseolus vulgaris ssp. Vulgaris var. Nanus) Until the formulation begins to drip, the specific active compound Spray an aqueous formulation containing 250 ppm. After growing the plants in the greenhouse for 7 days, The mortality of the thorny scale insects (growing population) was examined. Preparation of Examples B and C 100% mortality was found using the compound. Example 8: Action on housefly   The bottom and lid of the Petri dish are in each case a specific active compound. Is coated with 3 ml of an aqueous dilution of a stock wettable powder containing 250 ppm of Dry it After that, place the 24 hour old housefly (Musca domestica) in a Petri-dish and Seal with the treated lid. Check housefly mortality after 3 hours at room temperature of 20 ° C Was. Using compounds of compounds B and C, 100% killing was achieved. Example 9: Egg killing action (Manduca sexta)   Cover Petri dish with Jaan filter paper inside bottom and 20 Manduca sexta 1 day old egg on filter paper. Then add about 1 ml of synthetic insect food in a Petri dish. Test corresponding to 600 l / ha, in the heart and inside the bottom with eggs and food Spray a wettable powder aqueous suspension of the product. Petri-Dish sealed and at room temperature for 5 days Hold and measure egg mortality. Compound B showed 100% action. Example 10:   Activated compound dissolved in methanol to larvae (L4) of cockroach Blaberus craniifer Inject things. Application of the compounds according to Examples B and C (active ingredient 2 × 10^-Fourg / dynamic After 48 hours, 100% mortality was found. Example 11:   The active compound dissolved in acetone was added to the larvae (L4) of the cigarette tinctor Manduca sexta. inject. Application of the compounds according to Examples B and C (active ingredient 2 × 10^-Fourg / animal) After 48 hours, 100% mortality was found. Use as antiparasitic agent Example 12: In vitro test against tropical bovine tick (Boophilus microplus)   The activity of the compounds according to the invention against ticks was detected in the following test design .   To prepare suitable formulations of the active compound, the active compound is dissolved in dimethylforma Amide (85 g), nonylphenol polyglycol ether (3 g) and oxyethyl 10% (w / v) in a mixture consisting of hydrogenated castor oil (7 g) The emulsion concentrate thus obtained is diluted with water to a test concentration of 500 ppm.   In each case, 10 fully suffocated tropical ticks Boophilus microplus The filled females are immersed in these active compound dilutions for 5 minutes. Then tick the filter paper The back was fixed on an adhesive film for the purpose of drying on top and laying the eggs. Mites, Place in a heating cabinet at 28 ° C. and 90% atmospheric humidity.   As a control, female mites are immersed only in water. Spawning eggs two weeks after treatment Activity was evaluated using the light inhibition.   In this test, the compound according to Example C is in each case 500p At a concentration of active compound of pm, it showed 100% inhibition of egg laying. C. Manufacturing Examples Example A 4- [4- (1,1,3,3-tetramethylbutyl) -cyclohex-3-enoxy] -5,6,7, 8-tetrahydroquinazoline   0.46 g (15.3 mm) sodium hydride (80% strength dispersion in mineral oil) Mol) is converted to 4-[(1,1,3,3-tetramethyl) butyl]-in 20 ml of tetrahydrofuran. A solution of 2.3 g (11.2 mmol) of cyclohex-3-enol was added and the mixture was added to 3 parts. Heat under reflux for hours. After cooling to room temperature, it was dissolved in 5 ml of tetrahydrofuran. 1.7 g (10.2 mmol) of 4-chloro-5,6,7,8-tetrahydroquinazoline are added and The mixture was heated under reflux for a further 2 hours. After cooling to room temperature, isopropanol To the reaction solution and thereafter the mixture is stirred for 15 minutes and then methyl chloride Extracted with ren. The organic phase was dried and concentrated. For purification, the residue is: Chromatography on silica gel using petroleum ether / ethyl acetate 1 I understood. This gave 2.3 g (66% of theory) of a yellow oil. The oil gradually solidified. Preparation of 4- (4-alkylcyclohex-3-enylamino) pyrimidine Example Example B 4- [4- (1,1,3,3-tetramethylbutyl) -cyclohex-3-enylamino] -5- Chloro-6-ethylpyrimidine   Introduction K_TwoCO_Three 1.2 g (13.5 mmol) were introduced into 10 ml of dimethylformamide. 1.6 g of 4-[(1,1,3,3-tetramethyl) -butyl] -cyclohex-3-enylamine (9 mmol) was added and the mixture was stirred at 80 ° C. for 4 hours. Cooling for processing The reaction solution thus obtained was dissolved in water. The mixture is extracted with ether and the combined organic phases Washed with water, dried and concentrated. For purification, the residue was Chromatograph on silica gel using ter / ethyl acetate. this This gave 1.3 g (43.3% of theory) of a colorless oil. 4-[(1,1,3,3-tetramethyl) -butyl] -cyclohex-3-enyl Amine production   7 g of 4-[(1,1,3,3-tetramethyl) -butyl] -cyclohex-3-enone (33 At room temperature in the presence of 7 g of a molecular sieve (3Å) at room temperature. With 2.1 g (33 mmol) of sodium and 25.9 g (0.33 mol) of ammonium acetate Was stirred in 100 g of isopropanol for 72 hours. The reaction solution is filtered and the filtrate Was concentrated. The residue is dissolved in 15% strength NaOH and the mixture is_TwoCl_TwoExtracted in . The combined methylene chloride phase was extracted twice by stirring with dilute hydrochloric acid and then extracted. The combined hydrochloric acid phases were made basic with a 30% strength sodium hydroxide solution. The mixture Extracted with methylene chloride and the organic phase was dried and concentrated. 4.6 g of yellow oil ( 70% of theory). Production of 4-[(1,1,3,3-tetramethyl) -butyl] -cyclohex-3-enol   First, 4-[(1,1,3,3-tetramethyl) -butyl] -cyclohex-3-enone 1 0.0 g (48 mmol) was introduced into 60 ml of ethanol, and borohydride dissolved in 20 ml of water. 2.7 g (0.07 mol) of sodium hydrogen chloride were added dropwise and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated to dryness, the residue was dissolved in water and the mixture was added at 0 ° C. with 2N HCl To make it slightly acidic. It is extracted with ether and the combined ether phases are dissolved in saturated NaCl. Washed with liquid and dried. Concentrate to 7.1 g of product as a colorless solid (70 %), Which is reacted without further purification. Production of 4-[(1,1,3,3-tetramethyl) -butyl] -cyclohex-3-enone   First, 1-methoxy-4-[(1,1,3,3-tetramethyl) -butyl] -cyclohexyl 40 g (0.17 mol) of 1,4-diene in 500 ml of methanol Introduce 10% H_TwoSO_Four 600 ml are added dropwise at room temperature and the mixture is then stirred for 2 hours did. The reaction solution was poured into water and extracted with ether. The combined ether phases are_Two Washed with O and saturated NaCl solution and dried. 37 g of a colorless liquid by concentration (theory 99% of the value). This was reacted without further purification. 1-methoxy-4-[(1,1,3,3-tetramethyl) -butyl] -cyclohex-1,4-diene Manufacturing of   First, 4-[(1,1,3,3-tetramethyl) -butyl] -anisole 105 g (0.48 mol ) Was introduced into a mixture of 180 ml of tert-butanol and 120 ml of tetrahydrofuran. 1600 ml of ammonia were condensed at -78 ° C. 13.3 g (1.9 mol) lithium Was added in portions and then the mixture was refluxed for 1 hour. Reacts methanol and water The solution was slowly added. After evaporating off the ammonia, the residue was extracted with ether . The organic phase is washed with water, MgSO_FourDried above and concentrated. Colorless by this 95.8 g of liquid (90% of theory) were obtained. Without further purification Reacted. Production of 4-[(1,1,3,3-tetramethyl) -butyl] -anisole   First, 4-[(1,1,3,3-tetramethyl) -butyl] phenol 100 g (0.48 mol ) And K_TwoCO_Three 93.8 g (0.68 mol) were introduced into 260 ml of acetone. Dimethy sulfate 67 g (0.53 mol) were added dropwise to the reaction solution. When heat generation subsides, mixing The material was heated under reflux with stirring for 4 hours. 130 ml of acetone is distilled off and NH_FourOH 40m l is added and the mixture is then stirred for 10 minutes. Then add water to the reaction solution and mix The mixture was extracted with ether and the combined organic phases were washed with water, 2N NaOH and then saturated. Wash with aqueous NaCl solution and MgSO_FourDried on. 105 g of solid product by concentration (Theoretical value 98%) and was reacted without further purification. Preparation for 4- (1-aryl-1-cyclohexen-4-ylamino) -pyrimidine Example of construction Example C 5-chloro-6-ethyl-4- [1- (3-fluoro-4-methoxy-phenyl) -cyclo [Hexen-4-ylamino] -pyrimidine   1.6 g of 4-amino-1- (3-fluoro-4-methoxy-phenyl) cyclohexene 7 mmol), 1.2 g (7 mmol) of 4,5-dichloro-6-ethyl-pyrimidine and 1.4 g (14 mmol) of triethylamine were added under reflux for 10 hours in 5 ml of toluene. Heated. For treatment, the mixture is diluted with toluene and stirred with water Extracted by The organic phase was dried and concentrated. Residue for purification On silica gel using 7: 3 petroleum ether / ethyl acetate It was processed. This gave 0.6 g (27.6% of theory) of a colorless oil. This oil is Crystallized slowly. 86-87 ° C. Production of free amine 4-amino-1- (3-fluoro-4-methoxy-phenyl) cyclohexene   First, 1- (3-fluoro-4-methoxy-phenyl) -cyclohexene-4-o 10.1 g (46 mmol), ammonium acetate 35.5 g (0.46 mol) and 3Å molecules 17 g of sieve are introduced into 250 ml of isopropanol and sodium cyanoborohydride 2.9 g (46 mmol) were introduced in small portions at 0 ° C. with stirring. Mix the chamber Stir for 72 hours at room temperature, remove the solvent and remove the residue with methylene chloride / 2N sodium hydroxide. Thorium solution and one The mixture was extracted several times by stirring it. The combined methylene chloride phase is combined with diluted hydrochloric acid. The mixture is extracted twice by stirring and the combined hydrochloric acid phases are washed with 30% strength Basified with sodium solution. The mixture is extracted with methylene chloride and the organic phase Was dried and concentrated. 3.3 g (32.4% of theory) of the product were obtained as a yellow oil Was done. The oil gradually solidified. Preparation of 1- (3-fluoro-4-methoxy-phenyl) -cyclohexen-4-one   4-hydroxy-4- (3-fluoro-4-methoxy-phenyl) -cyclohexanone 101.0 g (0.36 mol) of ethylene ketal are added to a mixture of 500 ml of formic acid and 30 ml of water. Then, the mixture was stirred at room temperature for 24 hours. After removing formic acid, the residue was dissolved in methylene chloride. Dissolve and wash the mixture with sodium bicarbonate solution and water, dry and concentrate did. This gave 71 g (89.5% of theory) of a colorless solid. Furthermore The reaction was carried out without purification. 68-70 ° C. 4-hydroxy-4- (3-fluoro-4-methoxy-phenyl) -cyclohexanone Production of Tylene Ketal   100 g of 4-bromo-2-fluoroanisole in 350 ml of tetrahydrofuran (0.49 Mol) and 13 g (0.53 mol) of magnesium file into a Grignard solution. Built. Cyclohexane-1,4-dione monoethylene in 150 ml of tetrahydrofuran A solution of 64.0 g (0.41 mol) of the ketal was added dropwise at 20-30 ° C. Mix the chamber Stirred for 2 hours at warm and 2 hours under reflux. Pour it on ice and solid chloride Ammonium was added, the mixture was diluted with 500 ml of toluene and the organic phase was separated, Dried and concentrated. This gave 101 g (88% of theory) of a solid product. This was reacted without further purification. 126-128 ° C. Example D   0.36 g (12 mmol) of sodium hydride (80% strength dispersion in mineral oil) 1- (3-Fluoro-4-methoxy-phenyl) -4-hydro in 30 ml of lahydrofuran To a solution of 2.5 g (11 mmol) of xy-cyclohexene is added and the mixture is degassed with hydrogen. Heated under reflux for 2 hours until birth was over. After cooling to room temperature, 4,5-dichloro-6- 2.0 g (11 mmol) of ethyl-pyrimidine are added and the mixture is refluxed for an additional 6 g. Heated for hours. After removal of the solvent, the residue is taken up in water / methylene chloride and The phases were dried and concentrated. For purification, the residue is separated from 4: 1 petroleum ether / Chromatographed on silica gel using ethyl acetate. By this This gave 3.0 g (75.3% of theory) of a yellow solid. 63-64 ° C. Free form 1- (3-fluoro-4-methoxy-phenyl) -4-hydroxy-cyclohexe Manufacturing   1- (3-Fluoro-4-methoxy-phenyl) -cyclohexen-4-one 10.0 g (4 5 mmol) was dissolved in 100 ml of methanol and 0.9 g of sodium borohydride (23 (Mmol) at 0 ° C. After the mixture was stirred at room temperature for 1 hour, 5 ml were added, the solvent was removed and the residue was treated with 2N sodium hydroxide solution and Take up in methylene chloride. The organic phase was dried and concentrated. 7.4g of yellow solid 74.0% of theory). This was reacted without further purification.   Similarly, the following compound was obtained. Example E 4- (cis-4-tert-butyl-cyclohex-3-enyloxy) -quinazoline   Mp 56-57 ° C. Example F 5-chloro-6-ethyl-4- (cis-4-tert-butyl-cyclohex-3-enylamino ) -Pyrimidine   Colorless oil. Example G 5-bromo-6-ethyl-4- (cis-4-tert-butyl-cyclohex-3-enylamino ) -Pyrimidine   Colorless oil. Example H 5-chloro-6-ethyl-4- [4- (3,4-dimethylphenyl) -cyclohex-3-e Nylamino] -pyrimidine   Colorless oil. Example I 4- [4- (3-fluoro-4-methoxy) -phenyl-cyclohex-3-enyloxy B) -Quinazoline   82-83 ° C.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 239/42 C07D 239/42 Z 239/88 239/88 (81) Designated country EP (AT, BE, CH) , DE, DK, ES, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE), OA (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR) , NE, SN, TD, TG), AP (KE, MW, SD, SZ, UG), AL, AM, AU, BB, BG, BR, BY, CA, CN, CZ, EE, FI, GE, HU, IS, JP, KG, KP, KR, KZ, LK, LR, LT, LV, MD, MG, MK, MN, MX, NO, NZ, PL, RO, RU, SG, SI, SK, TJ, TM, TT, UA, UZ, VN. Im Kirschiggarten 24 (72) Inventor Zanft, Ulrich Germany Day-65719 Hofheim. Blulahinshu-Turase 8 (72) Inventor Cologne, Manfred Germany Day-55296 Lertsv Eyler. Traminerweg 8 (72) Inventor Leucille Ring, Data Bernd Germany Day 35510 Büttschach. Texturshutrase 103 (72) Inventor Bonin, Wuerner Germany Day 65779 Kerkheim. Im Schulzjönten 18

Claims (1)

[Claims] 1. Formula I Or a salt thereof.     In the above equation,     R¹Is hydrogen, halogen, (C₁-C_Four) -Alkyl, (C₁-C_Four) -Haloalkyl, (C_Three-C_Five ) -Cycloalkyl or (C_Three-C_Five) -Halocycloalkyl;     R^TwoAnd R^ThreeAre the same or different and independently of one another Rogen, (C₁-C_Four) -Alkyl, (C₁-C_Four) -Haloalkyl, (C_Three-C₈) -Cycloalkyl, (C_Three-C₈) -Halocycloalkyl, (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Haloalkoxy, (C₁-C_Four) -Alkoxy- (C₁-C_Four) -Alkyl, (C₁-C_Four) -Haloalkoxy- (C₁-C_Four) -Al Kill, (C₁-C_Four) -Alkoxy- (C₁-C_Four) -Haloalkyl, (C₁-C_Four) -Haloalkoxy- (C₁ -C_Four) -Haloalkyl, (C₁-C_Four) -Alkylamino, (C₁-C_Four) -Alkylthio, (C₁-C_Four ) -Alkylsulfinyl, (C₁-C_Four) -Alkylsulfonyl, (C₁-C_Four) -Haloalkyl Thio, (C₁-C_Four) -Haloalkylsulfinyl, (C₁-C_Four) -Haloalkylsulfonyl, (C₁-C_Four) -Alkylthio- (C₁-C_Four) -Alkyl, (C_Two-C_Four) -Alkenyl, (C_Two-C_Four) -Al Quinyl, (C₁-C_Four) -Alkoxycarbonyl, cyano, (C₁-C_Four) -Cyanoalkyl or Is thiocyano; or     R^TwoAnd R^ThreeTogether with the carbon atom to which they are attached A 5- or 6-membered homocyclic ring of the sum, wherein said ring is CH 5 if it is a 5-membered ring_Twoof Alternatively, it may contain an oxygen or sulfur atom or the ring may be a 6-membered ring Contains one or two nitrogen atoms in place of one or two CH units. And the ring may optionally have (C₁-C_Four) -Alkyl, (C₁-C_Four)- Haloalkyl, preferably trifluoromethyl, halogen, (C₁-C_Four) -Alkoxy Or (C₁-C_Four) -Haloalkoxy to one, two or three identical or different groups May be substituted), or     R^TwoAnd R^ThreeIs saturated 5-, together with the carbon atom to which they are attached, A 6- or 7-membered homocyclic ring, wherein the ring comprises one or two CH_TwoOxygen instead of radicals And / or sulfur and the ring may optionally contain one, two or Or three (C₁-C_Four)-Which may be substituted by an alkyl group);     A is CH or N;     X is NH, oxygen or S (O)_q(Where q = 0, 1 or 2);     E is a direct bond or a linear or branched (C₁-C_Four) -Alkandiyl group , Preferably a direct bond;     a and b are the same or different and are each independently of the numbers 0, 1, 2 or 3 (a and b are not simultaneously 0);     R^FourIs halogen, (C₁-C_Four) -Alkyl, (C_Three-C₇) -Cycloalkyl, (C₁-C_Four) -C Loalkyl, (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Haloalkoxy or optionally Is an optionally substituted phenyl;     v is 0, 1 or 2;     U is a direct single bond, oxygen, a group S (O)_y(Where y = 0, 1 or 2 Or the group NR⁶(Where R⁶Is hydrogen, (C₁-C_Four) -Alkyl or (C₁-C_Four) -Arco Xi));     V is a direct single bond, carbonyl or formula (Where Q is oxygen, sulfur or (C₁-C_Four) -Alkylimino, where T is oxygen, sulfur Or group NR⁶'And T' is (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Alkylthio or Is NR⁶'R⁶"And R⁶'And R⁶"Is the same or different and R⁶Means the above A group with righteousness); and     R^FiveIs an alkyl, alkenyl, alkynyl, optionally substituted Aryl, optionally substituted heterocyclyl, cyano , Halogen, nitro, alkyloxyimino or group SiR⁷R⁸R⁹(Where R⁷and R⁸Is (C₁-C_Four) -Alkyl and R⁹Is alkyl, cycloalkyl, aryl or Or arylalkyl).     And R^FiveAlkyl, alkenyl, alkynyl or alkyl mentioned for Oxyimino group, R⁷, R⁸And R⁹The following features, if appropriate: i. One or more, preferably up to three non-adjacent CHs_TwoThe groups are CO and Or) heteroatom units such as O, S (O)_y(Where y = 0, 1 or 2), NR⁶ '' 'Or SiR⁷'R⁸'(Where R⁶'' 'Is R⁶And has the significance given above for R⁷'And And R⁸'Is R⁷And R⁸Has the meaning described above for); ii. 3 to 12 atoms of this group form a ring of up to 12-members; iii. The group is optionally halogen, alkyl, cycloalkyl,   Aryl, aryloxy, arylthio, heterocyclyl, heterocyclyl Oxy, heterocyclylthio, haloalkyl, arylalkyl, cycloalkyl Alkyl, alkoxy, haloalkoxy, alkylthio, cycloalkoxy, Alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, Chloroalkylalkanoyloxy, aroyloxy, arylalkanoyloxy Si, alkylsulfonyloxy, arylsulfonyloxy, heterocyclylca Rubonyloxy, hydroxyl, cyano and nitro (substituted The cycloaliphatic, aromatic or heterocyclic ring system in is unsubstituted or up to 3 ( The same or up to the highest number) in the case of halogen, preferably fluorine One or more from the system consisting of Preferably up to three (in the case of halogen, up to the highest number) identical or different May be substituted by the group   Has at least one feature of 2. R^FourIs halogen, preferably fluorine, chlorine and bromine, (C₁-C_Four) -Alkyl, (C₁ -C_Four) -Haloalkyl, (C₁-C_Four) -Alkoxy, (C₁-C_Four) -Haloalkoxy or (C₁- C_Four) -Alkylthio; and     R^FiveBut (C₁-C₂₀) -Alkyl, (C_Two-C₂₀) -Alkenyl, (C_Two-C₂₀) -Alkynyl, Optionally substituted aryl, optionally substituted Heterocyclyl, cyano, halogen, hydroxyl, carboxyl, nitro B, (C₁-C₂₀) -Alkyloxyimino or group SiR⁷R⁸R⁹(Where R⁷And R⁸Is (C₁- C_Four) -Alkyl and R⁹Is (C₁-C₂₀) -Alkyl or optionally substituted Aryl which may be optionally substituted);     And R^FiveAlkyl, alkenyl, alkynyl or alkyl mentioned for Oxyimino group, R⁷, R⁸And R⁹However, where appropriate, the following features:   i. One or more, preferably up to three non-adjacent CHs_TwoThe groups are CO and ( Or) heteroatom units such as O, S (O)_y(Where y = 0, 1 or 2), N R⁶'' 'Or SiR⁷'R⁸'(Where R⁶'' 'Is R⁶And has the significance given above for R⁷' And R⁸'Is R⁷And R⁸Has the meaning described above for R;   ii. 3 to 8 atoms of these groups form a ring of up to 8 members;   iii. The group is optionally halogen, (C₁-C₁₂) -Alkyl, (C_Three-C₈) -Cyclo Alkyl, aryl, aryloxy, arylthio, heterocyclyl, hetero Cyclyloxy, heterocyclylthio, (C₁-C₁₂) -Haloalkyl, aryl- (C₁- C_Four) -Alkyl, (C_Three-C₈) -Cycloalkyl- (C₁-C_Four) -Alkyl, (C₁-C₁₂) -Alkoki Si, (C₁-C₁₂) -Haloalkoxy, (C₁-C₁₂) -Alkylthio, (C_Three-C₈) -Cycloalco Kishi, (C₁-C₁₂) -Alkanoyloxy, (C₁-C₁₂) -Haloalkanoyloxy, (C_Three- C₈) -Cycloalkanoyloxy, (C_Three-C₈) -Cycloalkyl- (C₁-C₁₂) -Arkanoi Ruoxy, aroyloxy, aryl- (C₁-C_Four) -Alkanoyloxy, (C₁-C₁₂)- Alkylsulfonyloxy, arylsulfonyloxy, heterocyclylcarbo Nyloxy, hydroxyl, cyano and nitro (in these listed substitutions Cycloaliphatic, aromatic or heterocyclic ring systems are unsubstituted or up to 3 (halo (Preferably in the case of fluorine, preferably fluorine, and up to the highest number) One or more from the system consisting of Up to three (in the case of halogen May be substituted by up to the highest number of) identical or different groups and Other groups and variables are as described above; The compound of formula I or a salt thereof according to claim 1, having at least one feature of: 3. R¹Is hydrogen or fluorine;     R^TwoBut (C₁-C_Four) -Alkyl, cyclopropyl, halocyclopropyl, halo (C₁- C_Two) -Alkyl, methoxymethyl or cyano;     R^ThreeIs hydrogen, halogen, methyl, ethyl, methoxy, ethoxy, cyano or Is (C₁-C_Four) -Alkoxycarbonyl; or     R^TwoAnd R^ThreeTogether with the carbon atom to which they are attached, Or an optionally substituted unsaturated 5- or 6-membered ring (when the ring is a 5-membered ring, In, CH_TwoWhich can contain sulfur atoms instead of units). Or     R^TwoAnd R^ThreeTogether with the carbon atom to which they are attached form a saturated 5- Or a 6-membered ring wherein the ring is CH_TwoContain sulfur or oxygen atoms instead of units Can be formed);     A is CH or N;     X is NH or oxygen;     E is a direct bond;     a is the number 1 and b is the number 2;     R^FourIs hydrogen, (C₁-C_Four) -Alkyl, trifluoromethyl or (C₁-C_Four) -Arco Kishi;     3. The formula I according to claim 1, wherein the other groups and variables are as described above. Or a salt thereof. 4. R¹Is hydrogen;     R^TwoIs methyl, ethyl, propyl, isopropyl, 1-fluoroethyl, Trifluoromethyl, cyclopropyl or methoxymethyl;     R^ThreeIs halogen, methyl, ethyl, methoxy, ethoxy, cyano or (C₁- C_Four) -Alkoxycarbonyl; or     R^TwoAnd R^ThreeBut together with the ring system to which they are attached, quinazoline or Is a quinoline system, which is substituted on the carbocyclic moiety by fluorine. Can) or     R^TwoAnd R^ThreeBut, together with the carbon atom to which they are attached, Membered ring (the ring is CH_TwoCan contain oxygen or sulfur atoms instead of radicals) Make;     v is 0;     U is a direct bond or oxygen;     A compound of formula I according to any of claims 1 to 3, wherein V is a direct bond or Is its salt. 5. R¹Is hydrogen;     R^TwoIs ethyl, propyl, isopropyl, 1-fluoroethyl, trifluoro Lomethyl or methoxymethyl;     R^ThreeIs fluorine, chlorine, bromine or methoxy;     Or, when A is nitrogen,     R^TwoAnd R^ThreeBut together with the ring system to which they are attached, the quinazoline system ( The system can be substituted by a fluorine atom), or     R^TwoAnd R^ThreeTogether with the ring system to which they are attached form 5,6,7,8-tetra Form a hydroquinazoline system;     A is CH or N;     X is NH or oxygen;     E is a direct bond;     a is the number 1 and b is the number 2;     v is 0;     U is a direct bond or oxygen; and     5. A compound of formula I according to any one of claims 1 to 4, wherein V is a direct bond or Is its salt. 6. R¹Is hydrogen;     R^TwoIs ethyl or methoxymethyl;     R^ThreeIs fluorine, chlorine, bromine or methoxy; or     If A = N, then R^TwoAnd R^ThreeTogether with the ring system to which they are attached To form a quinazoline or 5,6,7,8-tetrahydroquinazoline system;     R^FiveBut (C₁-C₂₀) -Alkyl, (C_Two-C₂₀) -Alkenyl or (C_Two-C₂₀) -Alkini [The three to six carbon atoms of these hydrocarbon groups are capable of forming a ring; (Or) these hydrocarbon groups are optionally unsubstituted or Up to 3 (in the case of fluorine and also up to the highest) identical or different substitutions May be substituted by a phenyl group which may have a moiety).     A is CH or N;     X is NH or oxygen;     E is a direct bond;     U and V together are a direct bond;     v is 0 and     The formula according to claim 1, wherein the other groups and variables are as described above. A compound of I or a salt thereof. 7. R^TwoIs methoxymethyl and R^ThreeIs methoxy, or     R^TwoIs ethyl and R^ThreeIs chlorine or bromine;     R^FiveBut (C₁-C₂₀) -Alkyl or (C_Two-C₂₀) -Alkenyl [of this group 3-6 The carbon atoms can form a ring and / or the group Unsubstituted or up to 3 (in the case of fluorine, also the highest number ) Substituted by a phenyl group which can have the same or different substituents May be used);     X is NH; and     The formula according to any one of claims 1 to 6, wherein the other groups and variables are as described above. A compound of I or a salt thereof. 8. Formula II  (Where A, R¹, R^TwoAnd R^ThreeHas the meaning described in formula I and L is A compound of formula III   (Where X, E, a, b, v, U, V, R^FourAnd R^FiveIs in formula I of claim 1 With the meaning described above) and, if appropriate, R^ThreeBut water If it is elementary, The compound of formula I obtained by another method is halogenated at the 5-position of the heterocyclic group. Or R in the side chain^FiveIs further derivatized and, where appropriate, obtained in this way. 8. A compound of formula I according to any one of claims 1 to 7, comprising converting the compound to a salt thereof. Preparation of the compound of 9. At least one compound according to any of claims 1 to 7 and at least A composition consisting of one formulation. Ten. 8. The composition according to claim 1, which comprises additives or auxiliaries customary for use. 10. A bactericidal active amount of at least one compound according to claim 9. Disinfecting composition. 11． 8. The composition according to claim 1, which comprises additives or auxiliaries customary for use. 10. The insecticidal or killing of claim 9 which comprises an active amount of at least one compound of claim 9. A tick, tickicidal or nematicidal composition. 12． 8. The composition according to claim 1, which comprises, together with auxiliaries and additives, customary for use. Bactericidal, insecticidal, acaricidal, tick-killing of at least one compound according to claim Or nematicidally active amounts and preferably fungicides, insecticides, attractants, infertility At least one other activity from a system consisting of a pesticide, an acaricide, a nematicide and a herbicide. A plant protection composition containing a sexual compound. 13. 8. The composition according to claim 1, which comprises, together with auxiliaries and additives, customary for use. Or in wood preservation containing an active amount of at least one compound according to claim Coolant wetting or drilling and cutting oils for closed compositions, paints, metalworking A composition for use as a preservative in water. 14. Contracts for use as veterinary medicine, preferably for controlling endo- and ectoparasites The compound according to any one of claims 1 to 7, or the compound according to claim 9, Composition. 15． Combine the active compound and other additives and convert them to the appropriate use form. 15. A method for producing a composition according to any one of claims 9 to 14, comprising: 16． A compound according to any one of claims 1 to 7 or a bactericide or a compound as claimed in claim 9, Use of the composition according to any one of claims, 12 and 13. 17． Cooling wetting agents as wood preservatives or for closed compositions, paints, metalworking Or as a preservative in drills and cutting oils. Use of a compound as described or a composition according to any of claims 9, 10 and 13. 18． A compound according to any one of claims 1 to 7, or any one of claims 9, 10 and 11. A bactericidal active amount of the composition according to any of the preceding claims, More invaded plants, plants consisting of applying to area or substrate or to seeds A method for controlling pathogenic bacteria. 19. A compound according to any one of claims 1 to 7, or any one of claims 9, 10 and 12. An active amount of the composition described in any of the preceding sections is applied to harmful insects, mites, mollusks and nematodes. Or application to plants, areas or substrates infested by these pests. To control harmful insects, mites, mollusks and nematodes. 20. 8. The method of claim 1 for controlling harmful insects, mites, molluscs and nematodes. 13. The compound according to any one of claims or the composition according to any one of claims 9, 10 and 12. use. twenty one. A compound according to any one of claims 1 to 7, or any one of claims 9, 10 and 12. A seed treated or coated with an active amount of the composition of any of the preceding claims.