JP2001514175A - Acylated 5-aminoisothiazoles as pesticides and fungicides - Google Patents

Abstract

(57) [Summary] The present invention relates to a compound of the formula (I) [Wherein R ¹ , R ² , R ³ , R ⁴ , A, Y and Z have the meanings mentioned in the detailed description. And a novel acylated 5-aminoisothiazole. The invention also relates to their production and their use in controlling pests and their use as fungicides.

Description

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to novel acylated 5-aminoisothiazoles, a process for their preparation and their use for controlling pests on animals and their use as fungicides .

It is already known that certain 5-aminoisothiazoles have insecticidal and / or fungicidal properties (for example WO 95/31448 and DE
-A 9542 372).

However, the potency and activity spectrum of these compounds is not always satisfactory, especially at low application rates and low concentrations.

Accordingly, the present invention provides a compound of formula (I)

[0005]

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Wherein R ¹ represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, alkylamino, dialkylamino or optionally substituted cycloalkyl; R ² represents hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkyl alkylsulfinyl, alkylsulfonyl, halogenoalkyl alkylsulfonyl, thiocarbamoyl, alkoxy, formyl, or represents alkylcarbonyl, or -CR ⁷ - NOR ^{8 wherein} R ⁷ and R ⁸ are each independently of the other hydrogen, alkyl, halogenoalkyl, alkenyl, optionally substituted cycloalkyl Represents alkyl or cycloalkylalkyl, or represents optionally substituted aryl or arylalkyl, respectively, wherein R ³ is alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, alkynyl, alkylcarbonyloxyalkyl, alkoxycarbonyloxy Represents alkyl; aryl optionally substituted,
Arylalkyl or aryloxyalkyl; cycloalkyl, each optionally substituted cycloalkylalkyl, or represents cycloalkyl alkoxyalkyl or cycloalkyl thio alkyl, or an -N = CR ⁵ R ^6, in which case R ⁵ and R Each of ⁶ independently of one another represents hydrogen, alkyl, halogenoalkyl, alkenyl, optionally substituted cycloalkyl or cycloalkylalkyl, or respectively represents optionally substituted aryl or arylalkyl, Or R ⁵ and R ^{6 taken} together with the carbon atom to which they are attached, represent an optionally substituted carbocyclic ring; R ⁴ is an optionally substituted aryl, an optionally substituted cycloalkyl Represents an optionally substituted cycloalkenyl, or Optionally represents an optionally substituted heterocyclic ring, A represents an oxygen or sulfur, Y is alkylene optionally substituted respectively, alkenylene or alkyleneoxy, and Z represents oxygen or sulfur. ] The present invention provides a novel acylated 5-aminoisothiazole.

Furthermore, the compounds of the formula (I) are:

[0008]

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Wherein each of R ¹ , R ² , R ⁴ and Y is the same as defined above. Compound formula ^{(III) R 3 -A-CZ} -G (III) [ wherein the, each R ^3, A and Z are the same as defined above, and G is a leaving group such as halogen (Especially chlorine) or imidazolyl. Or b) a compound of the formula (IV)

[0010]

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Wherein ^each of R ¹ , R ² , R ³ , A and Z is the same as defined above.
] In the formula (V) R ⁴ -Y-CO-G (V) wherein R ⁴ , Y and G are the same as defined above. In each case in the presence of a base and, where appropriate, in the presence of a diluent.

Finally, the novel compounds of the formula (I) have very remarkable biological properties, are particularly suitable as fungicides and agriculture, forestry, storage products and materials It has been found that it is suitable for controlling pests on animals, especially insects, spiders and nematodes, encountered in the field of sanitation and in the field of hygiene.

Surprisingly, the acylated 5-aminoisothiazoles according to the invention have considerably better activity against pests and fungi on animals compared to known compounds of similar structure. are doing.

Formula (I) provides a general definition for the compounds of the present invention.

Preferred substituents and ranges of groups described in the formulas referred to in the above-mentioned parts and the following parts are described below.

[0016] R¹ Is preferably C₁ -C_Four Alkyl, 1 to 5 identical or different halo
C containing a gen atom (eg, a fluorine, chlorine or bromine atom)₁ -C_Four Halogeno archi
Le, C₁ -C_Four Alkoxy-C₁ -C_Four Alkyl, C₁ -C_Four Alkylthio-C ₁ -C_Four Alkyl, C₁ -C_Four Alkoxy, C₁ -C_Four Alkylthio, C₁ -C _Four Alkylamino, di (C₁ -C_Four Alkyl) amino or C₁ -C_Four 
The same or from the group consisting of alkyl or halogen (eg fluorine, chlorine or bromine)
Optionally mono- or tri-substituted C with different substituents_Three -C₆ Cycloalkyl
Represent.

R^Two Is preferably hydrogen, halogen, cyano, nitro, thiocyanato, C₁ −
C_Four Alkoxycarbonyl, C_Two -C_Four Alkenyloxycarbonyl, C₁ -C _Four Alkylthio, from 1 to 5 identical or different halogen atoms (eg fluorine or
C having a chlorine atom)₁ -C_Four Halogenoalkylthio, C₁ -C_Four Alkylsul
Finyl, one to five identical or different halogen atoms (eg fluorine or chlorine atoms)
C)₁ -C_Four Halogenoalkylsulfinyl, C₁ -C_Four Alkyls
Ruphonyl, one to five identical or different halogen atoms (eg fluorine or chlorine atoms)
C)₁ -C_Four Halogenoalkylsulfonyl, thiocarbamoyl, C₁ 
-C_Four Alkoxy, formyl, C₁ -C_Four Represents alkylcarbonyl, or-
CR⁷ = NOR⁸ Represents

Each of R ⁷ and R ⁸ independently of one another is preferably hydrogen, C ₁ -C ₄ alkyl, C ₁ -C 5 having the same or different halogen atoms (eg fluorine or chlorine atoms) ₁ -C ₄ halogenoalkyl, represents a C ₂ -C ₄ alkenyl; C ₃ -
Is C ₆ cycloalkyl or C ₃ -C ₆ cycloalkyl -C ₁ -C ₄ alkyl [each of which identical or different substituents from the group consisting of C ₁ -C ₄ alkyl and halogen (e.g. fluorine, chlorine or bromine) The group is optionally mono- or tri-substituted. Or phenyl or phenyl-C ₁ -C ₄ alkyl, each of which is optionally mono- or tri-substituted with the same or different substituents;
Possible substituents on the phenyl ring are in each case halogen, nitro, cyano,
C ₁ -C ₄ alkyl, C ₁ -C ₂ halogenoalkyl having ₁ to 5 identical or different halogen atoms (for example, fluorine or chlorine atom), C ₁ -C ₄ alkoxy,
C ₁ -C ₄ alkylthio, C ₁ -C ₂ halogenoalkoxy and C ₁ -C ₂ halogenoalkylthio, in each case from 1 to 5 identical or different halogen atoms (eg fluorine or chlorine atoms), C _1- C ₄ alkoxycarbonyl and C ₁
—C ₄ alkylcarbonyloxy. ].

R^Three Is preferably C₁ -C₈ Alkyl, 1 to 5 identical or different halo
C having a gen atom (eg, a fluorine or chlorine atom)₁ -C_Four Halogenoalkyl, C ₁ -C_Four Alkoxy-C₁ -C_Four Alkyl, C₁ -C_Four Alkylthio-C₁ -C _Four Alkyl, C_Two -C_Four Alkenyl, C_Two -C_Four Alkynyl, C₁ -C_Four Archi
Lecarbonyloxy-C₁ -C_Four Alkyl, C₁ -C_Four Alkoxycarbonyl
Kishi-C₁ -C_Four Represents alkyl; phenyl, phenyl-C₁ -C_Four Alkyl
Is phenoxy-C₁ -C_Four Alkyl [each of which has the same or different phenyl ring
Is optionally mono- or tri-substituted with different substituents; possible substituents are
Logen, nitro, cyano, C₁ -C_Four Alkyl, 1 to 5 identical or different
C having a halogen atom (for example, a fluorine or chlorine atom)₁ -C_Two Halogenoalkyl
, C₁ -C_Four Alkoxy, C₁ -C_Four Alkylthio, one or more in each case
C having five identical or different halogen atoms (eg, fluorine or chlorine atoms)₁ −
C_Two Halogenoalkoxy and C₁ -C_Two Halogenoalkylthio, C₁ -C_Four Al
Coxycarbonyl and C₁ -C_Four Alkylcarbonyloxy. ]
Or C_Three -C₆ Cycloalkyl, C_Three -C₆ Cycloalkyl-C₁ -C_Four Al
Kill, C_Three -C₆ Cycloalkoxy-C₁ -C_Four Alkyl or C_Three -C₆ Cyclo
Alkylthio-C₁ -C_Four Alkyl [each of these is C₁ -C_Four Alkyl
Identical or different members from the group consisting of and halogens (eg, fluorine, chlorine or bromine)
The substituent is optionally mono- or tri-substituted. Or -N = CR^Five R⁶ Represents

R^Five And R⁶ Are preferably, independently of each other, hydrogen, C₁ -C_Four A
Alkyl, 1 to 5 identical or different halogen atoms (eg fluorine or chlorine atom
C)₁ -C_Four Halogenoalkyl, C_Two -C_Four Represents alkenyl; C_Three −
C₆ Cycloalkyl or C_Three -C₆ Cycloalkyl-C₁ -C_Four Alkyl [this
Each of them is C₁ -C_Four Alkyl and halogen (eg fluorine, chlorine or bromine
Optionally mono- or tri-substituted with the same or different substituents from the group consisting of
I have. Or phenyl or phenyl-C₁ -C_Four Alkyl [these
Each is optionally mono- or tri-substituted with the same or different substituents,
Possible substituents on the phenyl ring are in each case halogen, nitro, cyano
, C₁ -C_Four Alkyl, 1 to 5 identical or different halogen atoms (eg, fluorine
C having a hydrogen atom or a chlorine atom)₁ -C_Two Halogenoalkyl, C₁ -C_Four Alkoxy
, C₁ -C_Four Alkylthio, in each case 1 to 5 identical or different groups
C having a halogen atom (eg, a fluorine and chlorine atom)₁ -C_Two Halogenoalkoxy
And C₁ -C_Two Halogenoalkylthio, C₁ -C_Four Alkoxycarbonyl and C ₁ -C_Four Alkylcarbonyloxy. Or R^Five And R⁶ Is, together with the carbon atom to which it is attached, C₁ -C_Four Alkyl,
C₁ -C_Four The group consisting of alkoxy and halogen (eg fluorine, chlorine or bromine)
5 or more members which are optionally mono- or tri-substituted by the same or different substituents
Represents a 7-membered carbocyclic ring.

R ⁴ is preferably C ₃ -C ₈ cycloalkyl or C ₄ -C ₈ cycloalkenyl, each of which is optionally mono- or polysubstituted with the same or different substituents, and group, Table halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ halogenoalkyl, C ₁ -C ₄ halogenoalkoxy, a hydroxyl and C ₁ -C ₄ alkylcarbonyl.) Or phenyl, wherein the phenyl is optionally mono- or penta-substituted (preferably mono- or tri-substituted) with the same or different substituents, and possible substituents are halogen,
Nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ halogenoalkyl, C ₁ -C ₄ halogenoalkoxy, C ₁
-C ₄ halogenoalkylthio, hydroxyl -C ₁ -C ₄ alkyl, C ₁ -C ₄
Alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylcarbonyloxy, amino, C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkylcarbonylamino, di (C ₁ -C ₄₎ alkylamino, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ halogenoalkyl alkenyloxy, identical or different halogen optionally mono- or polysubstituted C ₄ -C ₆ cycloalkenyl oxy substituents; and phenyl, phenoxy, phenylthio, benzyl , Pyridinyloxy, pyrimidinyloxy, thiazolyloxy or thiadiazolyloxy (each of which is optionally mono- or tri-substituted with the same or different substituents; possible substituents are halogen, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C _1-
C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, amino thiocarbonyl, aminocarbonyl, C ₁ -C ₄ alkoxyimino -C ₁ -C ₄ alkyl, C ₁ -C ₄ halogenoalkyl, C ₁ -C ₄ halogenoalkoxy and C ₁ -C ₄ -halogenoalkylthio. ). Or optionally mono- or tri-substituted with the same or different substituents, and has 1 to 3 heteroatoms (eg, N, S and O atoms), and as a ring member 5- or 6-membered heterocycle, which may include a CO group, for example

[0022]

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Where R⁹ Is C₁ -C_Four Alkyl, such as especially methyl or ethyl;
C₁ -C_Four Alkylcarbonyl, such as especially methylcarbonyl or ethylcarboxyl
Represents bonyl; or phenylsulfonyl (which is C₁ -C_Four Alkyl, for example
If especially methyl or ethyl; halogen, for example especially fluorine or chlorine; C₁ -C_Four 
Halogenoalkyl, for example, especially trifluoromethyl; C₁ -C_Four Alkoxy,
For example, especially methoxy; and C₁ -C_Four Halogenoalkoxy, for example, especially tri
Optionally monosubstituted with the same or different substituents from the group consisting of fluoromethoxy,
Is disubstituted. And possible substituents are halogen, nitro, cyano, C₁ -C_Four Alkyl, C₁ -C_Four 
Alkoxy, C₁ -C_Four Alkylthio, C₁ -C_Four Halogenoalkyl, C₁ -C _Four Halogenoalkoxy, C₁ -C_Four Halogenoalkylthio, phenylsulfonyl
(This phenylsulfonyl is represented by C₁ -C_Four Alkyl, halogen, C₁ -C_Four Halo
Genoalkyl, C₁ -C_Four Alkoxy and C₁ -C_Four Made of halogenoalkoxy
Optionally mono- or disubstituted by the same or different substituents from the group. )
And phenyl, phenoxy, phenylthio or benzyl (each of which is
Mono- or tri-substituted by the same or different substituents, and possible substituents
Is halogen, nitro, cyano, C₁ -C_Four Alkyl, C₁ -C_Four Alkoxy,
C₁ -C_Four Alkylthio, C₁ -C_Four Halogenoalkyl, C₁ -C_Four Halogenoa
Lucoxy and C₁ -C_Four Halogenoalkylthio. ).

A preferably represents oxygen or sulfur.

Y is preferably C ₁ -C ₆ alkylene, C ₁ -C ₆ hydroxyalkylene,
C ₁ -C ₄ alkoxy-C ₁ -C ₆ alkylene, C ₁ -C ₄ alkylcarbonyloxy-C ₁ -C ₆ alkylene, cyano-C ₁ -C ₆ alkylene, 1 to 5 identical or different halogen atoms C ₁ -C ₄ with (eg fluorine or chlorine atoms)
Halogenoalkyl alkylene, C ₃ -C ₆ cycloalkyl -C ₁ -C ₄ alkylene, C ₂
-C ₄ alkenylene or C ₁ -C ₄ alkyleneoxy, each of which is optionally mono- or tri-substituted with the same or different substituents from the group consisting of fluorine, chlorine and methyl.

Halogen preferably denotes fluorine, chlorine and bromine.

[0027] Z preferably represents oxygen or sulfur.

R ¹ is particularly preferably methyl, ethyl, n- or i-propyl, n-, i
-, s-or t- _{butyl; CH 2 F, CHF 2,} CF 3, CH 2 Cl, CH 2 B
r, CHClCH ₃ ; methoxy, ethoxy, methylthio, methylamino, methoxymethyl, ethoxymethyl; methylthiomethyl or cyclopropyl.

R ² is particularly preferably hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, n-
Propoxycarbonyl; allyloxycarbonyl; CSNH ₂ , SCH ₃ , SO
CH ₃ , SO ₂ CH ₃ , CHO, COCH ₃ , CH ＝ NOCH ₃ or C (CH ₃
) = NOCH ₃ .

R ³ is particularly preferably methyl, ethyl, n- or i-propyl, n-, i
-, s-or t- butyl, n- pentyl, n- hexyl, n- heptyl, n- octyl; C ₁ -C ₂ having one to five identical or different halogen atoms (e.g. fluorine or chlorine atom) halogenoalkyl, C ₁ -C ₂ alkoxy -C ₁ -C ₂ alkyl, C ₁ -C ₂ alkylthio -C ₁ -C ₂ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₂ Represents alkylcarbonyloxy-C ₁ -C ₂ alkyl, C ₁ -C ₂ alkoxycarbonyloxy-C ₁ -C ₂ alkyl; or phenyl, phenyl-C ₁ -C ₂ alkyl or phenoxy-C ₁ -C ₂ alkyl (In each of these, the phenyl ring is optionally mono- or tri-substituted with the same or different substituents, and possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trif Oromechiru, methoxy, ethoxy, methylthio,
Trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl or methylcarbonyloxy. Or cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally mono- or tri-substituted in which the cycloalkyl moiety is the same or different and the Do substituent represents methyl, ethyl, n- or i- propyl, fluorine, or represents chlorine and bromine.), or -N = CR ⁵ R ^6.

Each of R ⁵ and R ⁶ independently of one another particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; or phenyl Or phenyl-C ₁ -C ₂ alkyl (each of which is optionally mono- or tri-substituted on the phenyl ring with the same or different substituents; possible substituents are fluorine, chlorine, bromine, nitro, cyano , Methyl, ethyl, trifluoromethyl,
Methoxy, ethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl or methylcarbonyloxy. Or R ⁵ and R ⁶ together with the carbon atom to which they are attached, particularly preferably with the same or different substituents from the group consisting of methyl, ethyl, methoxy, fluorine and chlorine Represents a mono- or disubstituted 6-membered carbocyclic ring.

R^Four Is particularly preferably cyclopentyl, cyclohexyl, cyclopentenyl
Or cyclohexenyl, each of which is optionally substituted with the same or different substituents.
Monosubstituted to pentasubstituted (preferably monosubstituted or disubstituted) and possible substituents
Is fluorine, chlorine, bromine, methyl, ethyl, isopropyl, methoxy, trifluoro
Lomethyl and methylcarbonyl. Or phenyl [where the phenyl is mono- or optionally substituted with the same or different substituents
Trisubstituted and possible substituents are fluorine, chlorine, nitro, cyano; methyl, d
Tyl, n- or i-propyl, n-, i-, s- or t-butyl;
Toxy, n- or i-propoxy, methylthio; -CF_Three , -CHF_Two , -CH _Two CF_Three , -CH_Two -CF_Two -CHF_Two , -CH (CF_Three ) -CH_Three ; -OCF _Three , -OCHF_Two , -OCH_Two CF_Three , -O-CH_Two -CF_Two -CF_Three , -OC
H_Two -CF_Two -CHF_Two , -O-CH (CF_Three ) -CH_Three ; -SCF_Three ; -CH _Two OH; methylcarbonyl, ethylcarbonyl; methoxycarbonyl, ethoxy
Carbonyl; methylcarbonyloxy, ethylcarbonyloxy; amino, methyl
Ruamino, dimethylamino, methylcarbonylamino;

[0033]

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And phenyl, phenoxy or phenylthio, each of which is optionally mono- or disubstituted with the same or different substituents, wherein the possible substituents are fluorine,
Chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methylsulfinyl, methylsulfonyl, methylcarbonyl, aminothiocarbonyl. ). Or the following heterocyclic ring

[0035]

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[Each of these heterocycles is optionally mono- or disubstituted with the same or different substituents, the possible substituents being in each case fluorine, chlorine, nitro, cyano; methyl, ethyl , n- or i- propyl, n-, i-, s- or t- butyl; methoxy, ethoxy, n- or i- propoxy; methylthio; -CF _3, -
_{CHF 2, -CH 2 CF 3,} -CH 2 CF 2 -CHF 2, -CH (CF 3) -C
_{H 3; -OCF 3, -OCHF 2} , -OCH 2 CF 3, -O-CH 2 -CF 2 -
CF ₃ , —OCH ₂ —CF ₂ —CHF ₂ , —O—CH (CF ₃ ) —CH ₃ ;
CF ₃ ; and phenyl, phenoxy or phenylthio, each of which is optionally mono- or disubstituted with the same or different substituents, the possible substituents being fluorine, chlorine, nitro, cyano, methyl, ethyl, . methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy and trifluoromethylthio), where, R ⁹ is, C ₁ -C ₄ alkyl, such as, in particular methyl or ethyl; C ₁
-C ₄ alkylcarbonyl, for example, or especially methyl carbonyl or ethylcarbonyl; or phenylsulfonyl (the phenyl sulfonyl C ₁ -C ₄ alkyl, such as, in particular methyl or ethyl; halogen, such as, in particular fluorine or chlorine; C ₁ -C ₄ halogenoalkyl, such as, in particular trifluoromethyl; C ₁ -C ₄
Alkoxy, such as, in particular methoxy; and and C ₁ -C ₄ halogenoalkoxy, For example, in particular mono- or di-substituted with identical or different substituents from the group consisting trifluoromethoxy. ). ] Represents one of the following.

A particularly preferably represents oxygen or sulfur.

Y is particularly preferably a group: —CH_Two -, -CH (CH_Three )-, -CH (C_Two H _Five )-, -CH (n-C_Three H₇ )-, -CH (i-C_Three H₇ )-, -CH_Two CH _Two -, -CH (OH)-, -CH (OCH_Three )-, -CH (O-CO-CH_Three )
-, -CH (CN)-, -CHF-, -CHCl-,

[0039]

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Represents one of —CH ＝ CH— or —CH ₂ O—.

Z particularly preferably represents oxygen or sulfur.

R¹ Is very particularly preferably methyl, ethyl, n- or i-propyl, n-
, I-, s- or t-butyl; CH_Two F, CHF_Two , CF_Three , CH_Two Cl, CH _Two Br, methoxy, ethoxy, methylthio, methylamino or cyclopropyl
Represent.

R ² is very particularly preferably hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, CSNH ₂ , SCH ₃ , SOCH ₃ , SO ₂ C
H ₃ , CHO, COCH ₃ , CH ＝ NOCH ₃ or C (CH ₃ ) ＝ NOCH ₃ .

R ³ is very particularly preferably methyl, ethyl, n- or i-propyl, n-
Chloroethyl; 2,2,2-trifluoroethyl; methoxymethyl, methoxyethyl; allyl, propargyl; phenyl or benzyl (each of which has the same or different phenyl ring The substituents are optionally mono- or disubstituted with substituents, and possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methoxycarbonyl, ethoxy Carbonyl or methylcarbonyloxy) or cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl
(Each of which cycloalkyl moiety is methyl, it is mono- or di-substituted with identical or different substituents from the group consisting of fluorine and chlorine.) Or represents; or -N = CR ⁵ R ⁶ Represents

Each of R ⁵ and R ⁶ independently of one another is very particularly preferably methyl,
Represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl; or phenyl or benzyl, each of which is optionally mono- or disubstituted with the same or different substituents on the phenyl ring. Substituted, possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy,
Ethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl and methylcarbonyloxy. ).

R^Four Is very particularly preferably phenyl, which is optionally monosubstituted
To tri-substituted (preferably mono- or di-substituted), and possible substituents are
Xy, ethoxy, i-propoxy; -OCF_Three , -OCHF_Two , -OCH_Two CF _Three , -OCH_Two CF_Two CF_Three , -OCH_Two CF_Two CHF_Two , -OCH (CH_Three )
-CH_Three And optionally fluorine, chlorine, trifluoromethyl, methyl, methoxy,
Methylthio, methylsulfinyl, methylsulfonyl, aminothiocarbonyl,
Phenoxy substituted with nitro or cyano. Or the following heterocyclic ring

[0047]

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[These heterocycles are methoxy, ethoxy, —OCF ₃ , —OCH ₂ CF ₃ , —O
_{CH 2 CF 2 CF 3, -OCH} (CF 3) -CH 3 or optionally fluorine, chlorine,
Optionally substituted with phenoxy substituted with nitro or cyano. ]].

A very particularly preferably represents oxygen.

Y is very particularly preferably —CH_Two , -CH (CH_Three )-, -CH (OCH _Three )-Or -CH (OCOCH_Three )-.

Z very particularly preferably represents oxygen.

Preferred compounds of the present invention have the formula (IA) or (IB), or (IC):

[0053]

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Wherein ^each of R ¹ , R ² , R ³ , A, Y and Z has the above-mentioned general, preferred, particularly preferred and very particularly preferred meanings, and X ¹ , X ² , X ^3, each of X ⁴ and X ^5, generally the phenyl and phenoxy group under item R ^4, preferred, particularly preferred and represent a very particular substituents described above as preferred, also X ^1, X each ^2, X ³ and X ^4, it may represent an additional hydrogen. ] It is a substance of.

A further preferred group of compounds is that wherein the phenoxy group is N (CZ-AR ³
) -CO-CH ₂ - or ^{N (CZ-AR 3) CO} -CH (CH 3) - Formula (IA) is para to group a compound of (IB) or (IC), these Particularly preferred among the compounds are those wherein the substituents X ¹ , X ² , X ³ and X ⁴ represent hydrogen.

The definitions or descriptions of the general or preferred radicals given above apply not only to the final product but also to the corresponding starting materials and intermediates. The definitions of these groups can be combined with one another as desired, ie also within their respective preferred ranges.

According to the present invention, preference is given to compounds of the formula (I) which contain a combination of the definitions mentioned above as being preferred.

According to the present invention, a compound of formula (I) comprising a combination of the above-mentioned particularly preferred definitions
Are particularly preferred.

According to the invention, very particular preference is given to compounds of the formula (I) which contain a combination of the definitions mentioned above as being very particularly preferred.

In the definitions of the groups mentioned above and in the parts mentioned below, a hydrocarbon group such as alkyl or alkenyl, even if bonded to a heteroatom such as alkoxy or alkylthio, is in each case as straight-chain as possible. Or branched.

In the group definitions given above, alkyleneoxy or —CH ₂ O— is to be understood as connecting R ⁴ in formula (I) to the oxygen of this alkyleneoxy or —CH ₂ O— group. is there.

In particular, besides the preparation examples, the following compounds of the formula (I) can be mentioned: Table 1

[0063]

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The compounds in Table 1 are: R ¹ ＣC ₂ H ₅ ; R ² = chlorine;

[0065]

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Y = CH ₂ and —CZ-A—R ³ corresponds to the general formula (I) in which the substituents are listed below.

[0067]

[Table 1]

[0068] Table 2 Table 2 compounds have the general formula R ^2, R ^4, Y and -CZ-A-R ³ with an R ¹ = CH ₃ is the same as listed in Table 1 (I
).

The compounds of Table 3 Table 3, the general formula R ² together are _{^{R 1 = i-C 3 H}} 7, R 4, Y and -CZ-A-R ³ are the same as listed in Table 1 (I
).

The compounds of Table 4 Table 4,

[0071]

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And wherein R ² , R ⁴ , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0073] Table Compound 5 Table 5 is generally R ^1, R ^4, Y and -CZ-A-R ³ with an R ² = Br is the same as listed in Table 1 Formula (I
).

The compounds of Table 6 Table 6, generally R ¹ together with an ^{R 2 = CN, R 4,} Y and -CZ-A-R ³ are the same as listed in Table 1 Formula (I
).

The compounds in Table 7 Table 7, the general formula R ^1, R ^4, Y and -CZ-A-R ³ with an R ² = -COOCH ₃ are the same as listed in Table 1 (I
).

The compounds of Table 8 Table 8, R ^1, R ^4, Y and -CZ-A-R ³ with an R _² = -COOC ² H ₅ is the same as listed in Table 1 the general formula ( I
).

The compounds in Table 9 Table 9, the general formula R ^1, R ^4, Y and -CZ-A-R ³ with an R ² = SCH ₃ is the same as listed in Table 1 (I
).

The compounds of Table 10 Table 10 Formula R ^1, R ^4, Y and -CZ-A-R ³ with an R ² = SOCH ₃ is the same as listed in Table 1 (I
).

The compounds of Table 11 Table _{11, Y = -CH (CH 3)} - R 1, R 2, R 4 and -CZ-A-R ³ with an are the same as listed in Table 1 General formula
This corresponds to (I).

The compounds of Table 12 Table _{12, Y = -CH (OCH 3)} - R 1, R 4, R 2 and -CZ-A-R ³ with an are the same as listed in Table 1 General formula
This corresponds to (I).

The compounds of Table 13 Table _{13, Y = -CH (OCOCH 3)} - R 1, R 2, R 4 and -CZ-A-R ³ with an are the same as listed in Table 1 General formula
This corresponds to (I).

The compounds of Table 14 Table 14,

[0083]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

The compounds of Table 15 Table 15,

[0086]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

The compounds of Table 16 Table 16,

[0089]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

The compounds of Table 17 Table 17,

[0092]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

The compounds of Table 18 Table 18,

[0095]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

The compounds of Table 19 Table 19,

[0098]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

The compounds of Table 20 Table 20,

[0101]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0103] The compounds of Table 21 Table 21,

[0104]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0106] The compounds of Table 22 Table 22,

[0107]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0109] The compounds of Table 23 Table 23,

[0110]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0112] Table compounds of Table 24 24,

[0113]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0115] The compounds of Table 25 Table 25,

[0116]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0118] The compounds of Table 26 Table 26,

[0119]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0121] The compounds of Table 27 Table 27,

[0122]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0124] The compounds of Table 28 Table 28,

[0125]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0127] The compounds of Table 29 Table 29,

[0128]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0130] The compounds of Table 30 Table 30,

[0131]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0133] The compounds of Table 31 Table 31,

[0134]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0136] The compounds of Table 32 Table 32,

[0137]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0139] The compounds of Table 33 Table 33,

[0140]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0142] The compounds of Table 34 Table 34,

[0143]

Embedded image

And wherein R ¹ , R ² , Y and -CZ-A-R ³ are the same as those listed in Table 1.
).

[0145] The compounds of Table 35 Table 35,

[0146]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0148] The compounds of Table 36 Table 36,

[0149]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0151] The compounds of Table 37 Table 37,

[0152]

Embedded image

And wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1.
).

[0154] The compounds of Table 38 Table 38,

[0155]

Embedded image

Wherein R ¹ , R ² , Y and —CZ-A—R ³ are the same as those listed in Table 1
).

[0157] Compounds of Tables 39 to 63 Tables 39 to 63 is, R ^1, R ^2, Y and -CZ-A-R ³ are the same as listed in Table 2, listed R ⁴ are in Table 14-38 A general formula that is the same as
This corresponds to (I).

[0158] Compounds of Tables 64 to 88 Tables 64 to 88 is, R ^1, R ^2, Y and -CZ-A-R ³ are the same as listed in Table 3, enumeration R ⁴ are in Table 14-38 A general formula that is the same as
This corresponds to (I).

[0159] Compounds of Tables 89 to 113 Tables 89 to 113 has, R ^1, R ^2, Y and -CZ-A-R ³ are the same as listed in Table 4, enumeration R ⁴ is In Table 14-38 This corresponds to the general formula (I) which is the same as described above.

Tables 114 to 138 The compounds in Tables 114 to 138 have the same R ¹ , R ² , Y and -CZ-A-R ³ as listed in Table 5, and R ⁴ is listed in Tables 14 to 38. This corresponds to the same general formula (I) as described above.

[0161] Compounds of Tables 139 to 163 Tables 139 to 163 is, R ^1, R ^2, Y and -CZ-A-R ³ are the same as listed in Table 6, listed R ⁴ is In Table 14-38 This corresponds to the general formula (I) which is the same as described above.

[0162] Compounds of Tables 164 to 188 Tables 164 to 188 is, R ^1, R ^2, Y and -CZ-A-R ³ are the same as listed in Table 7, enumeration R ⁴ is In Table 14-38 This corresponds to the general formula (I) which is the same as described above.

[0163] Compounds of Tables 189 to 213 Tables 189 to 213 is, R ^1, R ^2, Y and -CZ-A-R ³ are the same as listed in Table 8, enumeration R ⁴ is In Table 14-38 This corresponds to the same general formula (I) as described above.

Tables 214 to 238 The compounds in Tables 214 to 238 have the same R ¹ , R ² , Y and -CZ-A-R ³ as listed in Table 9 and R ⁴ in Tables 14 to 38. This corresponds to the general formula (I) which is the same as described above.

Tables 239 to 263 The compounds shown in Tables 239 to 263 are those in which R ¹ , R ² , Y and —CZ-A—R ³ are as shown in Table 10.
And corresponding to general formula (I) wherein R ⁴ is the same as listed in Tables 14-38.

According to method (a), for example, N- (4-chloro-3-methyl-
When using 5-isothiazolyl) -4- (4-cyanophenoxy) phenylacetamide and methyl chloroformate, the course of the process according to the invention can be represented by the following reaction scheme:

[0167]

Embedded image

According to method (b), for example, when 4-chloro-5- (isopropoxycarbonylamino) -3-methylisothiazole and 4- (4-cyanophenoxy) phenylacetyl chloride are used as starting materials, Can be represented by the following reaction formula:

[0169]

Embedded image

Most of the compounds of the formula (II) required as starting materials for carrying out the process (a) according to the invention are known (see WO 95/31448, DE 95 42 372) and / or It can be manufactured in a customary manner.

The compounds of the formula (III) to be further used as starting materials in the process (a) according to the invention are widely known compounds belonging to the organic chemistry.

The compounds of the formula (IV) required as starting materials for carrying out the process (b) according to the invention are new and form part of the subject of the present invention. They have the formula (VI)

[0173]

Embedded image

[Wherein each of R ¹ and R ² is the same as defined above. Can be obtained by reacting the 5-aminoisothiazoles with the compound of the formula (III) according to the method (a).

The 5-aminoisothiazoles of the formula (VI) are mostly known (for example DE
-A 43 28 425, DE-A 22 49 162, WO-A 93 /
19045, WO-A 94/21 617 and J.I. Het. Chem. 19 89 can be produced by 26,1575 reference) and / or their known methods (see, eg, the cited references.) Formula (VI A)

[0176]

Embedded image

Embedded image wherein R ¹ is as defined above, and R ^2-1 represents R, —CO—R ^7-1 or —CR ^7-1 ＮＯNOR ⁸ . (In that case,
R is alkylthio, halogenoalkylthio, represents alkylsulfinyl, halogenoalkyl alkylsulfinyl, the R ² in the meaning of alkylsulfonyl and halogenoalkyl alkylsulfonyl, R ^7-1 is hydrogen or alkyl, preferably C ₁ -C ₄ alkyl, e.g. , Especially methyl, and R ⁸ is the same as defined above. 5-aminoisothiazoles are novel and also part of the subject matter of the present application.

The 5-aminoisothiazoles of the formula (VI A) can be obtained in a widely known manner according to the following general scheme (for this, see also the Preparation Examples):

[0179]

Embedded image

In formulas (VI B) to (VI H), each of R ¹ , R ⁸ and R has the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.

The 5-aminoisothiazoles of the formula (VI B) are known (for example, see
Het. Chem. 1989 , 26, 1575) and / or they can be produced by known methods.

Further compounds of the formula (V) used as starting materials for the process (b) according to the invention are widely known compounds belonging to organic chemistry.

The methods (a) and (b) described above for preparing compounds of formula (I)
It is preferably performed in the presence of a diluent. Suitable diluents are all customary solvents. Preference is given to using optionally halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles, such as cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.

The processes (a) and (b) described above for preparing compounds of formula (I) are carried out in the presence of a base (Chem. Ber. 98 , 829 (1965); Liebi).
gs Ann. Chem. 739, 201 (1970) and 636 (1973)
See also

Suitable bases for processes (a) and (b) are all customary proton acceptors.
It is preferred to use alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates or bicarbonates or nitrogen bases. Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate,
Triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN
) And diazabicycloundecene (DBU).

In the detailed methods (a) and (b), the reaction temperature can be varied within a relatively wide range. Generally, the reaction is carried out between -40 ° C and + 200 ° C, preferably at -10 ° C.
It is performed at a temperature of from 100C to 100C.

When carrying out the processes (a) and (b) described above for preparing compounds of the formula (I), usually 1 to 2 mol per mol of the compound of the formula (II) or (IV), Preferably 1 to 1.5 mol of the compound of formula (III) or (V) is used.

The work-up and the isolation of the end products are carried out by generally known methods.

The active compounds are useful for controlling pests on animals, especially insects, spiders and nematodes, encountered in the protection of agriculture, forestry, stored products and materials and in the field of hygiene. It is suitable and exhibits excellent plant resistance as well as favorable toxicity for warm-blooded animals. They can preferably be used as plant protection agents. They are active against normally susceptible and resistant races, as well as at all or some stages of development. The above-mentioned pests include the following: From the order of the Isopoda, for example, Oniscus
asellus), Armadillidium vulg (Armadillidium vulg)
are) and Porcellio scaber; from Diplopoda, for example, Braniurus gutlatas (Bl)
aniulus guttulatus; from Chilopoda, for example, Geofilus carpofagus (G)
eophilus carpophagus and Scutigera
ra spec. ); From the tying class (Symphyla), e.g. Scatigelella imacurata (Scu
tigerella immaculatea; from the order of the Thyssanura, for example, Lepshima saccharina (Lepis)
ma saccharina); from the order of the Collembola, for example, Onichurus almus
(Onychiurus armatus); from the order of the Orthoptera, for example, Blatter Orientalis (Bl)
atta orientalis, Periplaneta
americana), Leucophaea m.
aderae), German cockroach (Blattella germanic)
a), Acheta domesticus, Glylotalpa spp., Locusta locust
igratria migratrioides, Melanoplus diferentialis, and Sistocerca gregaria; from the order of the Dermaptera ul. Curitermes (Reticul)
items spp. ); From the louse (Anoplura), for example, a person lice (Pediculus)
humanus corporis, Hemimatopinu
s spp. ) And furry white lice (Lignognatus spp.); From the order of the mosquitoes (Mallophaga), for example, the furry whiteflies (Trichod)
ectes spp. ) And Damarinea spp. From the order of the Thysanoptera, for example, the Clebaine zebra (Herc)
inothrips femorilis and thrips thrips (Thrips)
tabaci); from the order of the Heteroptera, for example, the brown stink bug (Euryg)
aster spp. ), Dysdercu intermedius
s intermedius, Piesma qua
drata), bedbugs (Cimex lectulararius), Rhodnius prolixus and triatoma (T
riatoma spp. ); From the order of the Homoptera, for example, Aleurodes brassicae (Ale)
urodes brassicae), Whiteflies (Bemisia ta)
baci), Trialeurodes Vaporariolmes (Trialeurodes)
vaporariorum, cotton aphid (Aphis gossypiii)
), Radish aphids (Brevicoryne brassicae), Cryptomyzus livis, Aphis fabae, apple aphids (Aphis pomi)
), Apple beetle (Eriosoma lanigerum), peach aphid (Hyalopterus arundinis), Filoccera
Busttrix (Phylloxera vastatrix), Penfigus (Pemphigus spp.), Wheat beetle aphid (Macro)
siphum avenae), Aphid aphid (Myzus spp.), hoploa aphid (Phorodon humuli), wheat leaf aphid (Rhopalosiphum padi), Japanese leafhopper (Empoas)
ca spp. ), Eucelis bilobs
atus), leafhopper leafhopper (Nephotettix cincticep)
s), beetle scale insects (Lecanium corni), olive mold scales (Saissettia oleae), and ground beetle (Lao)
delphax striatellas, brown planthopper (Nilapar)
v. lugens) and the red-tailed scale insect (Aonidiella a)
urantii) and white-spotted scale insects (Aspidiotus heder)
ae), Pseudococcus spp., and psyllids (Psylla spp.); from the order of Lepidoptera, for example, Pectino
phor gossypiella), Bpulse Pinialius (Bupal)
us pinaria, Cheimatobi
a brumata), Lithocolletis bran caldera (Lithocolle)
tis blankcardella, Hyponomouta Padera (Hypono)
meuta padella), Plutella maculipe (Plutella maculipe)
nnis), Sea stalk beetle (Malakosoma neustria), Kwanokinushimushi (Eupractis chrysorrhoea), Gypsy moth
(Lymantria spp.), Buccaratrix sliveriella (Bu)
cculatrix thurberella), Citrus scuttlefish (Phy
locnistis citrella, noctuid (Agrotis spp.
), Euxoa spp., Feltia spp.
. ), Ealias insulana, Heliothis spp., Spodoptera exigua (Spod)
optera exigua), and a caterpillar (Mamestra brassi)
cae), Panolis flamemaea, Spodoptera litura, Spodoptera litura (Spodop)
tera spp. ), Trichoplusia ni (Trichoplusia ni)
), Carpocapsa pomonella,
Green beetle (Pieris spp.), Nikameichiyu (Chilo spp.
), Awanomeiga (Pyrausta nubilalis), Suzikonamamadameiga (Ephessia kuehniella), Honeybee (Galle)
ria mellonella, Tineola Viselliera (Tineola)
bisselliella), Tinea pellila
onella), Hofmannopira Pseudospletella (Hofmannop)
hila pseudospretella, Cacoesia podana (Caco
ecia podana), Capua reticulana
ana), Choristoneura fu
miferana), Clysia ambigue
lla), Homona magnanima and Tortrix viridana; from the order Coleoptera, for example Anovium punctatum (An)
obium punctatum) and Rhizoper
the dominica), Bruchidi obtex
us obectus), Haricot beetle (Acanthosceli)
des obectus), Hytorrupes Vagyurs (Hylotrupe)
s bajulus, Agelastica aln
i), Leptinotarsa decelineta (Leptinotarsa dece)
mlineata), Phedon cochliae (Phaedon cochl)
eariae), Diabrotica (Diabrotica spp.), Psylliodes chrysocephala
, Nymphalid beetle (Epilachna varivevestis), Atmaria (Atomaria spp.), Sawtooth leaf beetle (Oryzae)
philus surinamensis, weevil (Anthonom)
us spp. ), Weevil (Sitophilus spp.), Otiolynx sulcatus (Otiorrhynchus sulcatus), weevil (Cosmopolites sordidus), shoot lynx asimilis (Ceuthorhynchus assimil)
, Hypera postica, Katsuobushimushi (De
rmestes spp. ), Trogoderma spp.
), Anthrenus (Anthrenus spp.), Atagenus (Attag)
enus spp. ), Flycatcher beetle (Lyctus spp.), Meligethes aeneus,
Ptinus spp. ), Niptus holoukas
leucus), Gibium pylloide
s), Tribium spp., Tenebrio molitor, Aphid beetle (Agri)
otes spp. ), Conoderus spp., Melolontha melonlonsa, Amphimalon solstitialis (Amphimalon solstitialis)
s) and Costetra zealandica
ica); from the order Hymenoptera, for example, pine wasp (Diprion)
spp. ), Hoplocampa spp., Lasius (L
asius spp. ), Monomorium phalao
nis) and wasps (Vespa spp.); from the order Diptera, for example, Aedes (Aedes spp.), Anopheles (Anopheles spp.), Culex (Culex spp.),
Drosophila melanogaster (Drosophila melanogaster)
, House fly (Musca spp.), And fly fly (Fannia spp.
), Calliphora erythroce
phala), flies (Lucilia spp.), obi flies (Chr
ysomya spp. ), Cuterebra spp.,
Horsefly (Gastrophilus spp.), Hippobosca (Hyppo)
bosca spp. ), Sand flies (Stomoxys spp.), Sheep flies (Oestrus spp.), And bullflies (Hypoderma spp.).
), Tabby (Tabanus spp.), Tania (Tannia spp.),
Kefly (Biobiotullanus), Ossinella frito (Osci)
nella frit), black flies (Phorbia spp.), red flies (Pegomia hyoscyamii), Seratitis capitata (Ceratitis capitata), fruit fly oleae (Dac)
us oleae) and chipuma paludos (Tipula paludos)
a); from the order of the flea (Siphonaptera), for example,
Xenopsylla cheops and Nagano flea (Ceratophyl)
rus spp. ); From Arachnida, for example, Scorpio Maurus
io maurus and Latrodictus mactans (Latrodictu)
s mactans); from the order of the Acarina, for example, Acarus si
ro), acarid mite (Argas spp.), a mite (Ornithodo)
ros spp. ), Red mites (Dermanyssus gallinae),
Eriophies rivis, Phyllocottruta oleivora, Bovine tick (Boo)
philus spp. ), The red tick (Rhipicephalus sp.)
p), Amblyoma (Amblyomma spp.), Ibama tick (Hyal
Omma spp. ), Tick (Ixodes spp.), Scorpion mite (Psoroptes spp.),
tes spp. ), Scaroptes spp., Dust mite (Taronemus spp.), Clover spider mite (Bryobia p.)
raetiosa), Citrus red spider mite (Panonychus spp.)
And Tetranychus spp.

As the plant parasitic nematodes, for example, the nematode (Pratylench)
us spp. ), Citrus nematode (Radopholus sim)
ilis), stem nematode (Ditylenchus dipsaci), tangerine nematode (Tylenchurus semipenetrans), cyst nematode (Heterodera spp.), Globodera
era spp. ), Root-knot nematode (Meloidogyne spp.)
, Nematodes (Apelenoides spp.), Nematodes (
Longidorus spp. ), Xifine
ma spp. ) And Trichodrus spp.
).

The compounds of the formula (I) according to the invention are distinguished by a particularly high insecticidal activity.

The compounds of the formula (I) according to the invention are useful for the preparation of phytopathogenic insects, such as the green peach aphid [Myzus persicae].
, Green leafhopper [green rice cicada (Nephotet)
ix cinctipes)], mustard beetle [mustard b
eetle (Phaedon cochlaeriae)] and larva [o
wlet moth (Spodoptera frugiperda)] can be used particularly successfully to control larvae.

The active compounds are solutions, emulsions, wettable powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension emulsions, active and impregnated natural and synthetic substances, and It can be changed to a usual preparation such as a fine capsule in a coalesced substance.

These formulations may be prepared in a known manner, for example, if appropriate with a surfactant, ie,
It is prepared using an emulsifying and / or dispersing agent and / or a foam former and mixing the active compound with a bulking agent, ie, a liquid solvent and / or a solid carrier.

When the extender used is water, for example, an organic solvent can be used as an auxiliary solvent. As the liquid solvent, mainly aromatic compounds such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic compounds such as chlorobenzenes, chloroethylenes or methylene chloride or chlorinated aliphatic hydrocarbons; cyclohexane or paraffins; Aliphatic hydrocarbons such as, for example, mineral oil fractions, mineral oils and vegetable oils; alcohols such as butanol or glycol and their ethers and esters;
Suitable are ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strong polar solvents such as dimethylformamide and dimethylsulfoxide and water.

Solid carriers include, for example, ammonium salts and ground natural minerals, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground, such as highly dispersible silica, alumina and silicates. Synthetic minerals are suitable. Examples of solid carriers for granules include calcite, marble, pumice,
Crushed and separated natural rocks such as sepiolite and dolomite, as well as synthetic granules composed of inorganic and organic coarse powders, and sawdust, coconut corn, corn cob and tobacco stems Granules consisting of organic substances are suitable. Emulsifier and / or
Examples of the foam-forming agent include nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters and polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, and aryl sulfones. Acid salts as well as protein hydrolysates are suitable.
Suitable dispersants are, for example, lignin sulfite waste liquor and methylcellulose.

Carboxymethylcellulose; natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Adhesives can be used in the formulation. Other suitable additives are mineral and vegetable oils.

Inorganic pigments, for example iron oxide, titanium oxide and Prussian blue; organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and trace amounts of iron, manganese, boron, copper, cobalt, molybdenum and zinc salts and the like. Element (trace n
colorants such as U.S.C.

The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 9%.
Contains 0% by weight of active compound.

The active compounds according to the invention can be other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, fungicides, growth regulators or herbicides. Can be present in the form of customary preparations and also in the form of use prepared from these preparations. Among them, examples of the insecticide include phosphates, carbamates, carboxylate, chlorinated hydrocarbons, phenylureas, and substances produced by microorganisms.

Examples of co-ingredients in the mixture are the following compounds: Fungicides: aldimorph, ampropylphosph
os), ampropylphosphos potasium
sium), andoprim, and anilazine
ne), azaconazole, azoxystrobin (a
zoxystrobin, benalaxyl, benodanil, benomyl, benzamacryl, benzamacryl, benzamacryl-isobutyl,
Bialaphos, binapacryl,
Biphenyl, bitatanol, blasticidin-S, bromoconazole (bro)
muconazole, bupirimate, butiobate, calcium polysulphide, capsimicin, captafol, captan carb, carpamine, captan, carpamine carvon), quinomethionate (qui)
nomethionate, clobenthiazono
ne), chlorfenazole, chloroneb (c
chloroneb), chloropicrin, chlorothalonil, clozolinate
nate), clozylacon, kufuraneb (cufra)
neb), cymoxanil, cyproconazole (cypr)
oconazole, cyprodinil, cyprofuram, debacarb, dichlorophen
), Dichlobutrazole, diclofluanid, diclomezine,
Dichloran, dietofencarb
arb), difenoconazole, dimethirimol, dimethomorph
), Diconizazole, diconazole-M (di
niconazole-M), dinocap, diphenylamine, dipyrithione
, Ditalimfos, dithianon
, Dodemorph, dodine, drazoxolone, edifenphos, epoxyconazole (epoxyc)
onazole), etaconazole, etirimol
(Ethirimol), etridiazole (etridiazole), famoxadone (famoxadon), fenapanil (fenapanil)
, Fenarimol, fenbuconazole (fenbuco)
nazole, fenfuram, fenitropan (fen)
itropan), fenpiclonil, fenpropidin, fenpropimorph
orph), fentin acetate, fentin hydroxide, ferbam (fer)
bam), ferimzone, fluazinam (fluaz)
inam), flumetover, fluoromid (fluo)
romide), fluquinconazole, flurprimidol, flusilazole (flusi)
lazole), flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum
minium), fosetyl-sodium, fthalide, fiberidazole, furalaxyl, furamepyr,
Furcarbonyl, fluconazole
zole), fluconazole-cis, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazole
), Imazalil, imibenconazole
zole), iminoctadine, iminoctadine
Albesylate (iminoctadine albesilate), iminoctadine triacetate
), Iodocarb, ipconazol
e), iprobenfos [Iprobenfos (IBP)], iprodione (i
prodone), irumamycin, isoprothiolane, isovaledi
one), kasugamycin, kresoxime-methyl (kres
Oxim-methyl), copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate,
Copper preparations such as copper oxide, copper oxine, and Bordeaux mixture, mancopper, mancozeb, maneb, meferimzone, mepanipirime, mepanipirime, mepanipirime Metalaxyl, metconazole, methasulphocarb, methofloxam (meth)
furoxam), metiram (metiram), metomeculam (metome)
clam), metsulphovax, mildiomycin, microbutanil
1), microclosin, nickel dimethyldithiocarbamate
hiocarbamate, nitrosal-isopropyl (nitrothal)
-Isopropyl), nuarimol, offurase, oxadixyl, oxamocarb, oxolinic acid
, Oxycarboxym, oxyfenthiin (ox)
yfenthiin), paclobutrazol, pefurazoate (pe)
furazoate, penconazole, pencycuron, phosdiphen, phomaricin, pipemarin, piperalin, polyoxin, polyoxol, poroxol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpoz, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, porpozol, ropoz, porpozol, porpoz, ropoz, ropoz).
, Procymidone, propamomob
carb), propanosine-sodium
), Propiconazole, propineb (prop)
ineb), pyrazophos, pyrifenox (pyr)
ifenox), pyrimethanil, pyroquilon (
pyroquinil), pyroxyfur, quinconazole, quintozen [quintozen]
zene (PCNB)], sulfur and sulfur preparations, tebuconazole, teclophthalam (teclof)
talam), technazen, tetocyclasis (tetc)
yclassis), tetraconazole, thiabendazole, thicyophene
n), thifluzamide, thiophanate-methyl
(Thiophanate-methyl), thiram, thioximid, tolclofos-m
etyl), tolylfluanid, triadimefon, triadimenol
, Triazbutyl, triazoxide
ide), trichlamide, tricyclazole (tr
iciclazole), tridemorph (tridemorph), triflumizole (triflumizole), triforine (triforine),
Triconazole, uniconazole, validamycin A, vinclozolin
clozolin, biniconazole, zarilamide, zineb, ziram
am), and Dagger G, OK-8705, OK-8801, α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,
2,4-triazole-1-ethanol, α- (2,4-dichlorophenyl) -β-fluoro-β-propyl-1H-1,
2,4-triazole-1-ethanol, α- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1,2
, 4-Triazole-1-ethanol, α- (5-methyl-1,3-dioxan-5-yl) -β-[[4- (trifluoromethyl) -phenyl] -methylene] -1H-1,2 , 4-triazole-1
-Ethanol, (5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5-
(1H-1,2,4-triazol-1-yl) -3-octanone, (E) -α- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide, isopropyl {2-methyl-1- [[[1- (4-methylphenyl) -ethyl]
-Amino] -carbonyl] -propyl} -carbamate, 1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazole-
1-yl) ethanone-O- (phenylmethyl) -oxime, 1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione, 1- (3,5-dichlorophenyl) -3- ( 2-propenyl) -2,5-pyrrolidinedione, 1-[(diiodomethyl) -sulfonyl] -4-methyl-benzene, 1-[[2- (2,4-dichlorophenyl) -1,3-dioxolan-2- Yl] -methyl] -1H-imidazole, 1-[[2- (4-chlorophenyl) -3-phenyloxiranyl] -methyl]
-1H-1,2,4-triazole, 1- [1- [2-[(2,4-dichlorophenyl) -methoxy] -phenyl]-
Ethenyl] -1H-imidazole, 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro -Methyl-1,3-thiazole-5-carboxanilide, 2,2-dichloro-N- [1- (4-chlorophenyl) -ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide, 2 , 6-Dichloro-5- (methylthio) -4-pyrimidinyl-thioshanate, 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide, 2,6-dichloro-N-[[4- (tri Fluoromethyl) -phenyl] -methyl] -benzamide, 2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole, 2-[(1 -Methylethyl) -sulfonyl] -5- (trichloromethyl) -1,
3,4-thiadiazole, 2-[[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranosyl] -amino] -4-methoxy-1H-pyrrolo [ 2
, 3-d] pyrimidine-5-carbonitrile, 2-aminobutane, 2-bromo-2- (bromomethyl) -pentanedinitrile, 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl -1H-inden-4-yl) -3-pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N- (isothioshanatomethyl) -acetamide, 2-phenylphenol (OPP) 3,4-Dichloro-1- [4- (difluoromethoxy) -phenyl] -1H-pyrrole-2,5-dione, 3,5-dichloro-N- [cyano-[(1-methyl-2-propynyl) ) -Oxy] -methyl] -benzamide, 3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile, 3- [2- (4-chlorophenyl) ) -5- ethoxy-3-isoxazolidinyl]
-Pyridine, 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1
H-imidazole-1-sulfonamide, 4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one, 8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1 , 4-Dioxaspiro [4,5] decane-2-methanamine, 8-hydroxyquinoline sulfate, 9H-xanthen-2-[(phenylamino) -carbonyl] -9-carboxylic hydrazide, bis- (1-methylethyl) -3-Methyl-4-[(3-methylbenzoyl)-
Oxy] -2,5-thiohendicarboxylate, cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazole-
1-yl) -cycloheptanol, cis-4- [3- [4- (1,1-dimethylpropyl) -phenyl-2-methylpropyl] -2,6-dimethyl-morpholine hydrochloride, ethyl [(4 -Chlorophenyl) -azo] -cyanoacetate, potassium bicarbonate, methanetetrathiol sodium salt, methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5 -Carboxylate, methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate, methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexanecarboxamide, N- ( , 6-dimethylphenyl) -2-methoxy -N- (tetrahydro-2-
Oxo-3-furanyl) -acetamide, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-
Oxo-3-thienyl) -acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -1,4,5,6 -Tetrahydro-2-pyrimidineamine, N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidineamine, N- (5-chloro-2-methylphenyl) -2-methoxy-N -(2-oxo-
3-oxazolidinyl) -acetamide, N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide, N- [2,2,2-trichloro-1-[(chloroacetyl) -amino] -ethyl] -Benzamide, N- [3-chloro-4,5-bis (2-propynyloxy) -phenyl] -N '
-Methoxy-methanimidamide, N-formyl-N-hydroxy-DL-alanine-sodium salt, O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate, O- Methyl S-phenylphenylpropyl phosphoramidothioate, S-methyl 1,2,3-benzothiadiazole-7-carbothioate, spiro [2H] -1-benzopyran-2,1 ′ (3′H) -iso Benzofuran]
-3'-one, bactericide: bronopol, dichlorophen
), Nitrapyrin, nickel dimethyldithiodicarbamate, kasugamycin, octilinone
n), furancarboxylic acid, oxytetracycline, probenazole (p
robenazole), streptomycin (streptomycin),
Tecloftalam, copper sulphate and other copper preparations, Insecticide / Acaricide / Nematicide: abamectin, AC 303 630, acephate
(Acephate), acrinathrin, alanicarb, aldicarb, alfamethrin, alphamethrin, amitraz, abamectin, AZ60541, azadiractin
irachtin), azinphos A, azinphos A
M (azinphos M), azocyclotin, Bacillus thuringiensis
), Bendiocarb, benfuracarb
acarb), bensultap, beta cyfluthrin (
betacyfluthrin, bifenthrin,
BPMC, brofenprox, bromophos A (
bromophos A), bufencarb, buprofezin, butocarboxin (butcarbox)
in), butylpyridabene, cadusafos, carbaryl, carbofuran, carbophenothion
othion), carbosulfan, cartapu (c
artap), CGA 157419, CGA 184699, chloetocarb, chloroethoxyphos (chloroethoxy)
fos), chlorfenvinphos, chlorfluazuron, chlormefos (chlorm)
ephos), chlorpyrifos, chlorpyrifos M, cis-resmethrin (cis-res)
methrin, clocithrin, clofentezin, cyanophos, cyanophos, cycloprothrin, cyfluthrin
), Cyhalothrin, cyhexatin (cyhexat)
in), cypermethrin (cypermethrin), cyromazine (cyro)
mazin), deltamethrin, demeton M (demeton)
M), demeton S (demeton S), demeton-S-methyl (dem
eton-S-methyl), diafenthiuron (diafenthiu)
ron), diazinon, diclofenthion (dich)
lofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron,
Dimethoate, dimethylvinphos
Vinphos), dioxathion, disulfoton
(Disulphoton), edifenphos (edifenphos), emamectin (emamectin)
), Esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos
, Etrimphos, fenamiphos, fenazaquin
), Fenbutatin oxide, fenitrothion, fenobukab
rb), phenothiocarb, phenoxycarb (
fenoxycarb), fenpropathrin
, Fenpyrad, fenpyroximate (fenpyro)
ximat), fenthion, fenvalerate (fen)
valerate, fipronil, fluazinam (fl
uazinam), flucycloxuron, flucythrinate, flufenoxuron (flu)
fenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate
e), fubfenprox, furatiocarb (fur)
athiocarb), HCH, heptenophos, hexaflumuron (hex)
aflumuron), hexitythiazox, imidacloprid, iprobenfos (ipro)
benfos), isazophos, isofenphos (iso)
fenphos, isoprocarb, isoxathion, ivermectin, lambda-cyhalothrin, lufenuron, lufenuron, melpham, melvam, melvam, sampa, melvam, melvam, melvam, melvam, melvam, melvam, melvam, malam vin, melam vin, melam vin, melam vin, チ メ
s), metaldehide, methcliphos (meth)
acrifos), methamidophos, methidathion, methiocarb, methomyl, methomyl, metolcarb, milbemectin, monocromphos
os), moxidectin, naled, NC184, NI25, nitenpyram
ram), omesoate, oxamyl, oxydemethon M, oxydeprophos (oxydep)
rofos), parathion A (parathion A), parathion M (parathi)
on M), permethrin, phensoate (phe
nthoate, folate, phosalo
ne), phosmet, phosphamidon
don), phoxim, pirimicarb
, Pirimiphos M, pirimiphos A
iphos A), pro-phenol phosphate (profenofos), promecarb (promecarb), propaphos (propaphos), propoxur (propoxur), Purochiofosu (prothiofos), Purosoeto (prothoat), pymetrozine (pymetrozin), pyraclofos (pyrachlophos), pyridaphenthion (Pyridaphe
nthion), pyresmethrin (pyresmethrin), pyrethrum (
pyrethrum), pyridaben, pyrimidifen (
pyrimidifen), pyriproxyfen
, Kuinaruhosu (quinalphos), RH 5992, salithion (salithion), Sebufosu (sebfos), silafluofen (silafluofen), Surufotepu (sulfotep), Surupurofosu (sulprofos), tebufenozide (tebufenozide), tebufenpyrad (tebuf
empirad), tebupirimimiphos, teflubenzuron, tefluthrin (tefluthr)
in), temephos, terbam, terbufos, tetrachlorvinvi
nphos), thiafenox, thiodicarb (thi)
odicarb), thiophanox, thiometon (t
hyomethon, thionazine, thuringiensin, tralomethrin
), Triarathen, triazophos
os), triazuron, trichlorfon (trichl)
orfon), triflumuron, trimesacarb (
trimethacarb, vamidothion, XMC, xylylcarb (xyly)
lcarb), YI5301 / 5302, zetamethrin
n).

It is also possible to mix with other known active compounds, for example herbicides, or with fertilizers and growth regulators.

The active compounds according to the invention can also be present in the form of their customary preparations, and also in the form of use prepared from these preparations, as a mixture with synergists. Synergists are compounds that increase the effect of the active compound without requiring that the synergist added itself be active.

The active compound content of the use forms prepared from the customary preparations can be varied within wide ranges. The active compound concentration in the use forms is between 0.0000001 and 9
It may be 5% by weight of active compound, preferably 0.0001 to 1% by weight.

The mixtures are used in a customary manner suitable for the use forms.

When used on sanitary pests and pests on stored products, the active compounds have a pronounced residual action on wood and clay and an excellent stability against alkalis on lime water-immersed substrates. There is a characteristic in sex.

The active compounds according to the invention are not only active against pests on plants, hygiene and storage products, but also in the field of veterinary medicine, animal parasites (ectoparasites) such as, for example, mites, spider mites and bark mite. It is also active against creatures (manage mites), mite mites, flies (stabs and licks), larvae of parasitic fly (parasitic fly), lice, hair lice, lice and fleas. These parasites include the following: From the order of the lice (Anoplurida), for example, Haemato
pinus spp. ), Bottom lice (Lignognatus spp.)
. ), Human lice (Pediculus spp.), Phthils (Phitru)
s spp. ) And Solenopottes spp .; Maliphagida and Amblyce suborders (Amblyce)
rina) and from the order of Ischnocerina, for example, Trimenopon spp., Menopon
spp. ), Trinoton (Trinoton spp.), Bovikola (Bov
icola spp. ), Werneckiella spp
. ), Lepicentron spp., Damarina (Da
malina spp. ), Bottom lice (Trichodictes sp.)
p. ) And Felicola spp .; Diptera and Nematocerina
And from the order Brachycerina, for example, Aedes (A)
edes spp. ), Anopheles spp.), Culex (Culex spp.), Blackfish (Simulium spp.), Yuushimurium (Eusimulium spp.), Phlebotoms (Phlebotom)
us spp. ), Lutzomiia spp., Nukaka
(Culicoides spp.), Chrysops spp
. ), Hybomitra spp., Acylotas (Atyl)
otus spp. ), Tabanus (Tabanus spp.), Flytopa (H
aematopota spp. ), Philippomyia
spp. ), Braura spp., Housefly (Musca)
spp. ), Fly (Hydroteaea spp.), Fly (Storm)
oxys spp. ), Haematobia spp., Morelia (Smallia spp.), Fly fly (Fannia spp.)
. ), House fly (Glossina spp.), Blow fly (Callip)
hora spp. ), Flies (Lucilia spp.), Obi flies (Chrysomya spp.), Wolfahrt (Wohlfahrt)
ia spp. ), Flies (Sarcophaga spp.), Sheep flies (Oestrus spp.), Cowflies (Hypoderma spp.),
Horsefly (Gasterophilus spp.), Hipobosca (Hippo)
bosca spp. ), Lipoptena spp. And Melophaggus spp .; from the order of the Phalaenopsis, for example Pulex
spp. ), Ctenocephalides spp
. ), Rat flea (Xenopsylla spp.) And Nagano flea (Cera)
tophylus spp. ); From the order of the Heteroptera, for example, bed bugs (Cimex)
spp. ), Triatoma spp., Rhodnius (Rho)
dnius spp. ) And Panstrongyrus
spp. ); From the order of the Blattarida, for example, Blatta orientalis, Blattella cockroach (Peripla)
neta americana, German cockroach (Blattellage)
rmanica) and Spella (Suppella spp.); Acaria (Acarida), and the order of the Metastigmata (M
etastigmata) and Mesostigmata (Mesostigmata)
), For example, a tick (Argas spp.), A mite (Ornith)
odorus spp. ), Otobius spp., Tick (Ixodes spp.), Amblyoma (Amblyomma spp.).
), Boophilus spp., Dermascentre (Der)
accelerator spp. ), Tick (Haemophysalis sp.)
p. ), Ibama tick (Hyaromma spp.), Carrion tick (Rhip
icephalus spp. ), Red mites (Dermanyssus spp.)
), Raillietia spp.), Mite (Pneum)
onyssus spp. ), Sternostoma sp.
p. ) And Varroa spp .; from the order of Actinedida (Prostigmata) and the order of Acaridida (Astigmata), for example, Acarapis spp.
a spp. ), Ornithocheletia s
pp. ), Mycotia spp., Psorelgathes (Psor)
ergates spp. ), Demodex spp., Trombicula spp., Ristrohorus (Listro)
phorus spp. ), Acarus spp., Tyrophagus spp., Caloglyphus
s spp. ), Hypodectes spp., Pterolichus spp., Pterolichus mite (Pso)
ropes spp. ), Cliooptes spp.)
, Otodictes spp., Sarcoptes (Sarco)
ptes spp. ), Notoedres spp., Nemidocoptes spp., Cytodites (Cytotes)
dates spp. ) And Laminosioptes
spp. ).

For example, those active compounds are known as Boophilus mic
(Rupulus), sheep flies (Lucilla cuprina) and cockroaches (Periplaneta americana).

The active compounds of the formula (I) according to the invention can be used, for example, in agriculture such as cattle, sheep, goats, horses, pigs, donkeys, camels, wild cattle, rabbits, chickens, turkeys, ducks, geese, honeybees. Productive livestock; for controlling dogs, cats, breeding birds and other pets such as fish in aquariums; and arthropods parasitic on so-called test animals such as hamsters, guinea pigs, rats and mice. Also suitable for. By controlling these arthropods, mortality and
The use of the active compounds according to the invention allows for more economical and simple animal management, since the reduction in production (for meat, milk, wool, skin, eggs, honey, etc.) should be reduced. .

The active compounds of the present invention can be prepared in a manner known in the veterinary art, for example, tablets, capsules,
Drinks, potions, granules, pastes, pills, feed-through
method) and by administration in the intestine in the form of suppositories, for example also by injection (intramuscular, subcutaneous, intravenous, intraperitoneal injection, etc.), transplantation, nasal administration, such as immersion or bathing, spraying , Pouring-on and polishing (s
In the form of potting-on, washing, sprinkling (powdering), active compounds such as collars, ear tags, tail tags, limb bands, bridles, marking devices, etc. It is used by parenteral administration with administration to the skin with the help of molded articles containing it.

For use in livestock, poultry, pets and the like, the active compounds of the formula (I) may be formulated with the active compound in an amount of from 1 to 80% by weight (for example, powders, emulsions, free flowing agents) The composition may be used directly or after being diluted 100- to 10,000-fold, or may be used as a chemical bath.

Furthermore, it has been found that the compounds of the formula (I) according to the invention have a strong insecticidal action against insects which destroy industrial materials.

By way of example and also preferred, the following insects may be mentioned, but are not limited to: Anobium punctatum, Xestobium rufovillosum, Petilinus
Pectinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini
obium carpini), Flycatcher beetle (Lyctus brown)
eus), Lyctus africanus, Lyctus planicolis, Lyctus linearis, Lactus pembesens (L)
yctus pubescens), Trogoxilone Aequale (Trogo)
xylon aequal, Mintes, Rugikoris (Minthes ru)
gicollis), Xyleborus spec., Tryptodendron spec., Apate monachus, Bostricus capsinus (Bostr)
ychus capucins), Heterobostrix bruneuus (Het)
erobostychus bruneus, sinoxylone (Sinox)
ylon spec. ), Dwarf Mushroom (Dinoderus min)
Utens); Insects of the Hymenoptera (Hymenopterons), for example, the wasp (Silex juvencus), the urocels gigas (Uro)
cerus gigas, Urocellus gigas taignus (Uroceru)
s gigas taignus and Uroceru
saugur); Insects of the order Isoptera (Termites), for example, Carotermes flavicolilis
), Cryptotermes brevis
, Heterotermes indicola
), Reticulitermes flavipes (Reticulitermes flav)
apes), Reticulitermes santonensis (Reticuliterme)
s santonensis), Reticulitermes lucifugus (Reticu)
littermes lucifugus, Masttermes darwiniensis, Zoothermopsis nevadensis, and the termites (Copterotermes formosanus), for example, the insects of the order Coptermes formosanus;
episma saccarina).

The industrial materials concerned here are preferably synthetic resins, adhesives, glues (siz)
es), paper and paperboard, leather, wood and processed wood products and non-living materials such as coating compositions. Wood and processed wood products are materials to be protected from insect attacks, with particular preference.

Wood and processed wood products which can be protected by the agents according to the invention or mixtures containing these agents include, for example, building boards, wooden beams, railway sleepers, bridge components,
Boat piers, wooden carriages, boxes, pallets, containers, telephone poles, wooden siding, wooden windows and doors, plywood, chipboards, fittings that are quite commonly used for house building or house fittings or It should be appreciated as meaning wood products.

The active compounds can be used as is, in the form of a concentrate or in the form of customary preparations such as powders, granules, solutions, suspensions, emulsions or pastes.

The formulations described above can be prepared in a manner known per se, for example, by adding the active compound to at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent,
They can be prepared by mixing with desiccants and UV stabilizers where appropriate, or with dyes and pigments and other processing aids where appropriate.

The pesticidal compositions or concentrates used for preserving wood and wood products derived from wood contain the active compounds according to the invention in a concentration of from 0.0001 to 95% by weight, in particular from 0.001 to 60% by weight. I do.

[0219] The amount of composition or concentrate used depends on the type of insect and on the occurrence and living environment. Optimal usage can be determined by a series of tests for each use. However, it is generally sufficient to use from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight, of the active compound, based on the material to be protected.

The solvents and / or diluents used are organic chemical solvents or solvent mixtures and / or
Or oily or oily low-volatile organic chemical solvents or solvent mixtures and / or polar organic chemical solvents or solvent mixtures and / or water and, if appropriate, emulsifiers and / or wetting agents.

Preferably used organic chemical solvents have an evaporation number above 35 and above 30 ° C.
Preferably, it is an oily or oily solvent having a flash point above 45 ° C. The aforementioned substances used as water-insoluble, oily or oily, low-volatile solvents are suitable mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably petroleum distillates, petroleum and / or alkylbenzenes. is there.

Mineral oil having a boiling range of 170 to 220 ° C., test benzine having a boiling range of 170 to 220 ° C., spindle oil having a boiling range of 250 to 350 ° C., boiling range of 160 to 280 ° C. Petroleum and aromatic compounds with a turpentine oil and the same are conveniently used.

In a preferred embodiment, a liquid aliphatic hydrocarbon having a boiling range of 180 ° C. to 210 ° C. or a high boiling point of an aromatic hydrocarbon and an aliphatic hydrocarbon having a boiling point of 180 ° C. to 220 ° C. Mixtures and / or spindle oils and / or monochloronaphthalene, preferably α-monochloronaphthalene, are used.

The oily or oily low-volatile organic solvents having an evaporation number of more than 35 and a flash point of more than 30 ° C., preferably more than 45 ° C., are converted to highly volatile or moderately volatile organic solvents. It can be partially replaced by organic chemical solvents. In that case, the solvent mixture has an evaporation number above 35, a flash point above 30 ° C., preferably above 45 ° C., and the insecticide / fungicide mixture is soluble in this solvent mixture. It must be present or emulsifiable.

According to a preferred embodiment, part of the organic chemical solvent or solvent mixture is replaced by an aliphatic polar organic chemical solvent or solvent mixture. For example, it is preferable to use an aliphatic organic chemical solvent containing a hydroxyl group and / or an ester group and / or an ether group such as glycol ethers, esters and the like.

The organic chemical binders used in connection with the present invention are known per se and include synthetic resins which can be diluted with water and / or soluble or dispersible or emulsifiable in the organic chemical solvents used. And / or binding drying oil (binding drying oi)
ls), especially hydrocarbon resins such as acrylic resins, vinyl resins (eg polyvinyl acetate), polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd or modified alkyd resins, phenolic resins, indene / coumarone resins. , A binder composed of or containing a physically drying binder mainly composed of silicone resin, drying vegetable oil and / or drying oil and / or natural resin and / or synthetic resin.

The synthetic resin used as the binder can be used in the form of an emulsion, a dispersion or a solution. 10% by weight of bitumen or bitumen as binder
It can also be used in amounts up to. Dyes, pigments, water repellents, odor modifiers and inhibitors or corrosion inhibitors known per se and the same can be additionally used.

According to the invention, the composition or concentrate preferably comprises at least one alkyd resin or modified alkyd resin and / or at least one dry vegetable oil as organic chemical binder. It is preferred to use alkyd resins having an oil content of 45% by weight or more, preferably 50 to 68% by weight, according to the invention.

All or a part of the above-mentioned binders can be replaced with a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent evaporation of the active compound as well as crystallization or precipitation. They are (10 of binder used)
It is preferred to replace 0.01 to 30% of the binder (based on 0%).

Examples of the plasticizer include phthalic acid esters such as dibutyl phthalate, dioctyl phthalate or benzyl phthalate; phosphoric acid esters such as tributyl phosphate; adipic acid esters such as di- (2-ethylhexyl) adipate; Consists of stearic acid esters such as butyl stearate or amyl stearate, oleic acid esters such as butyl oleate, glycerin ethers or glycol ethers of relatively high molecular weight, glycerin esters and p-toluenesulfonic acid esters It originates from a chemical species.

The fixing agent is mainly composed of, for example, a polyvinyl alkyl ether such as polyvinyl methyl ether or a ketone such as benzophenone or ethylenebenzophenone.

A possible solvent or diluent is in particular water and, if appropriate, a mixture with one or more of the abovementioned organic chemical solvents or diluents, emulsifiers and dispersants.

Particularly effective protection of wood is achieved by industrial large-scale impregnation methods, such as vacuum, double vacuum or pressure methods.

The ready-to-use compositions are:
If appropriate, it may further contain an insecticide, and if appropriate, one or more fungicides.

[0235] Possible additional admixtures are preferably the insecticides and fungicides mentioned in WO 94/29268. The compounds mentioned in this document clearly form part of the present application.

Particularly preferred mixed components which may be mentioned are chlorpyrif (chlorpyrip)
hos), phoxim, silafluofin (silafluof)
in), alphamethrin, cyfluthulin (cy)
flumethrin, cypermethrin, deltamethrin, permethrin
, Imidacloprid, NI-25, flufenoxuron, hexaflumuron
ron) and insecticides such as triflumuron, and epoxyconazole, hexaconazole (h).
exaconazole, azaconazole, propiconazole, tebuconazole
nazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, tolylfluanid
fluuanid), 3-iodo-2-propynyl-butylcarbamate, N-
Fungicides such as octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

The compounds of the present invention have potent microbicidal activity and can be used in practice for controlling unwanted microorganisms. The active compounds are suitable for use as crop protection agents, in particular as fungicides.

[0238] Fungicides are used to protect crops from Plasmodiphoromycetes (Pla
smodiophoromycetes), Oomycetes, Chitridiomycetes, Zygomycetes
mycetes), Ascomycetes, Basidiomycetes (Basi)
dimycetes) and used to control deuteromycetes.

[0239] Bactericides are used to protect crops in the family Pseudomonas.
nadaceae), Rhizobiaaceae, Enterobacteriaceae (E)
<RTIgt; interobacteriaceae), </ RTI> Corynebaceae (Coryneb)
acteriaceae) and Streptomycetes (Streptomycetes)
aceae).

Some non-limiting examples of fungi causing fungal, fungal, and bacterial diseases included in the generic names listed above are: Xanthomonas species, such as Xanthomonas oryzae
homonas campestris pv. oryzae); Pseudomonas species, for example, Pseudomonas spp.
domonas syringae pv. lacrymans); Erwinia species, such as Erwinia a
mylovora; Pythium species, for example, Pythium ul
phytophthora species, for example, Phytophthora
thora infestans); Pseudoperonospora species, for example, downy mildew fungus (Pseudoperonospora humuli or Pseudop)
plasmopara species, such as downy mildew (Plasmopa)
ramicola); Bremia species, such as lettuce downy mildew (Bremia lact)
ucae); a species of Peronospora, for example, downy mildew (Peronospo)
ra pisi or P.R. brassicae); Erysiphe species, for example, Erysiphe
sphaerotheca species, such as powdery mildew (Sph)
aerotheca fuliginea; Podosphaera species, for example, powdery mildew (Podos)
phaera leucotricha; Venturia species, for example, Ventricia i
Pyrenophora species, for example, Pyrenoph.
ora teres or p. Graminea) (Conidiospore type: Drech)
slera, synonym: Helminthosporium; species of Cochliobolus, for example, Cochl
iobolus sativus (conidiophore: Drechslera; synonym: Helminthosporium); Uromyces species, for example, Uromyces app.
peniculatus; Puccinia species, for example, Puccinia re
sclerotinia species, for example, Sclerotinia;
(Tinia sclerotirum); a species of the genus Tilletia, for example, Anetaceae smut (Tillet)
ia caries); a species of Stilago, such as Ustilago nud
a or Ustilago avenae); a species of Pelicularia, for example, Pellicurium
cularia sasakiii); Pyricularia species, such as blast fungus (Pyric)
ularia oryzae; Fusarium species, for example, Fusarium klummorbium (F)
usarium culmorum; Species of the genus Botrytis, for example, Botrytis
Septria species, for example, Septoria no.
dorum); Leptosperia species, such as Leptosphaeria nodorum; Cercospora species, such as Cercospora canesensis sp.
ria brassicae); and Pseudocercosporella species, such as Pseudocercosporella herpotrichoides (Pseudocercos).
porella herpotrichoids).

The fact that the present active compounds are well tolerated by plants in the concentrations required to control plant diseases makes it possible to treat above-ground parts of plants, growing and growing stems and seeds, and soil. I do.

In addition, they show a broad in vitro activity against phytopathogenic fungi.

When used as fungicides, the active compounds according to the invention can be used as such, in the form of their commercial preparations or in the form of use prepared therefrom, for example in the form of adjusted solutions (re
It can be used in dy-to-use solutions, suspensions, wettable powders, pastes, soluble powders, powders, and granules. They can be prepared by customary methods, such as wetting, spraying, atomizing.
), Spraying, foam spraying, application and the like. Furthermore, the active compounds can be applied by the ultra-low volume method, or the active compound preparation or the active compound itself can be injected into the soil. Plant seeds can also be treated.

When treating parts of plants, the active compound concentrations in the use forms can be varied within wide ranges: generally, the active compound concentration is from 1 to 0.0001% by weight.
, Preferably 0.5 to 0.001% by weight.

When treating seed, usually from 0.001 to 50 g per kilogram of seeds
, Preferably from 0.01 to 10 g of active compound are required.

When treating soil, an active compound concentration of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, is required at the treatment site.

The preparation and use of the active compounds according to the invention is illustrated by the following examples.

Manufacturing Example Example 1

[0249]

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(Method a) 0.18 g (5.90 mmol) of sodium hydride was added to tetrahydrofuran 1
To a solution containing 1.50 g (3.90 mmol) of 4-chloro-5- [4- (4-cyano) phenoxy] -phenylacetylamino-3-methylisothiazole in 5 ml at a time was added little by little. Stir at room temperature for 15 minutes. Thereafter, the solution was cooled to -5 ° C and allyl chloroformate 0.71 in 2 ml of tetrahydrofuran.
g (5.90 mmol) is added dropwise. After stirring at −5 ° C. for 4 hours,
An additional 0.18 g (1.50 mmol) of allyl chloroformate is added and the mixture is stirred at room temperature for 18 hours. The reaction mixture is mixed with 50 ml of water and the precipitate formed is filtered off. The crude product was recrystallized from cyclohexane / ethyl acetate to give a melting point of 126.
0.60 g of 4-chloro-5-N- [4- (4-cyano) phenoxy] -phenylacetyl-N- (2-propenyloxycarbonyl) amino-3-methylisothiazole at from 127 DEG C. to 127 DEG C. (theoretical 22%).

Embodiment 2

[0252]

Embedded image

(Method b, including the preparation of the starting material) At -10 ° C., 7.80 g (77.0 mmol) of triethylamine and then 10.6 g (97.5 mmol) of ethyl chloroformate were first added to methyl ethyl ketone 5-amino-4-chloro-3-methylisothiazole (WO
95/31448) to a solution containing 5.80 g (39.00 mmol). The reaction mixture is stirred at −5 ° C. for 2 hours, taken up in water and repeatedly extracted with ethyl acetate.

The organic phase was dried, concentrated under reduced pressure and the crude product was purified by silica gel chromatography using methylene chloride as eluent to give 4-chloro-5-N- (ethyloxycarbonyl) amino-3- 3.43 g (41% of theory) of methylisothiazole are obtained as an oil.

3.00 g (13.6 g) of this compound contained in 20 ml of dimethylacetamide
Mmol) in 4.20 g of sodium hydride in 20 ml of dimethylacetamide
(16.3 mmol) is added dropwise. The mixture is stirred at room temperature for 1 hour, a solution of 6.57 g (24.3 mmol) of 4- (4-cyanophenoxy) phenylacetyl chloride in 20 ml of dimethylacetamide is added dropwise at -10 DEG C. and the mixture is added. Stir first at −10 ° C. for 3 hours, then at 0 ° C. for another 2 hours. The reaction mixture is poured into a saturated NaHCO ₃ solution and the precipitated solid is filtered off.
When recrystallized from cyclohexane / ethyl acetate, it has a melting point of 138 ° C to 139 ° C.
-Chloro-5-N- [4- (4-cyano) phenoxy] phenylacetyl-N-
1.20 g (23% of theory) of (ethoxycarbonyl) amino-3-methylisothiazole are obtained.

According to the methods of the above examples and / or by general preparation procedures, the following compounds of the formula (I) are obtained: Table 1

[0257]

[Table 2]

*) Log P = logarithm of the partition coefficient of n-octanol / water to base 10 (H ₂ O
Determined by reverse phase high performance liquid chromatography analysis using / CH ₃ CN. ) Preparation Example of Novel 5-Aminoisothiazoles of Formula (VI A) (VI A-1)

[0259]

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9.20 g (0.0807 mol) of 5-amino-3-methylisothiazole are dissolved in 100 ml of methylene chloride and mixed with 20 ml of pyridine. 10.70 g (0.0887 mol) of 2,2-dimethylpropionyl chloride are added dropwise and the mixture is stirred at 25 ° C. for 18 hours. The reaction solution is extracted with a 10% strength HCl solution, the organic phase is dried and the solvent is eliminated in vacuo. Thus, 5- (2,2-dimethyl-propionylamino) -3-methylisothiazole 1 having a melting point of 258 ° C.
0.03 g (71% of theory) are obtained.

4.48 g (0.0280 mol) of bromine were added to 5- (2
, 2-dimethyl-propionylamino) -3-methylisothiazole 5.00 g
(0.025 mol) and the mixture is stirred at 25 ° C. for 18 hours. The reaction solution is washed with water, dried, and the solvent is removed under reduced pressure. Thus, the melting point 142
4-bromo-5- (2,2-dimethyl-propionylamino)-
6.60 g (95% of theory) of 3-methylisothiazole are obtained.

Under argon, 4-bromo-5- (2,2- in 40 ml of tetrahydrofuran
Dimethyl-propionylamino) -3-methylisothiazole 5.0 g (0.0
(170 mol) is cooled to -70 ° C and 32 ml (0.0510 mol) of a 1.6N n-butyllithium n-hexane solution are added dropwise. The mixture was stirred at -5 ° C for 1 hour, cooled again to -70 ° C and then at this temperature 4.80 g of dimethyl disulfide (0.
051 mol) is added dropwise. The mixture is allowed to warm to room temperature, mixed with 50 ml of water and repeatedly extracted with ether. Dry the collected organic phases and remove the solvent under reduced pressure. In this way, 5.0 g (93% of theory) of 5- (2,2-dimethylpropionylamino) -3-methyl-4-methylthioisothiazole are obtained.

1.75 g of 5- (2,2-dimethylpropionylamino) -3-methyl-4-methylthioisothiazole in 20 ml of 1N NaOH solution and 20 ml of methanol
(0.00590 mol) is heated under reflux for 18 hours. 100 ml of water
And extract repeatedly with ethyl acetate. Dry the collected organic phases and remove the solvent under reduced pressure. In this way, 0.56 g (54% of theory) of 5-amino-3-methyl-4-methylthioisothiazole (VIA-1) are obtained. δ ¹ H-NMR (CDCl ₃ ): 2.15, 2.42, 5.03 Example (VI A-2)

[0264]

Embedded image

Under argon, 4-bromo-5- (2,2 in 100 ml of tetrahydrofuran
-Dimethylpropionylamino) -3-methylisothiazole (Example (VI
7.60 g (0.0270 mol) was cooled to -70 ° C, and 1.6
43.2 ml (0.0675 mol) of a solution of N in n-butyllithium n-hexane are added dropwise. After 1 hour, 6.00 g (0.0810 mol) of dimethylformamide are added dropwise. The mixture is stirred at -70 ° C for 2 hours, then mixed with 50 ml of a 2N HCl solution and extracted repeatedly with ether. Dry the collected organic phases and remove the solvent under reduced pressure. In this way, 5.49 g (80% of theory) of 4-formyl-5- (2,2-dimethylpropionylamino) -3-methylisothiazole are obtained.

2.5 g (0.00980 mol) of 4-formyl-5- (2,2-dimethylpropionylamino) -3-methylisothiazole in 50 ml of ethanol was added to 1.00 g (0.0118 mol) of methoxyamine hydrochloride. ) And mix. After adding 5.9 ml (0.0118 mol) of a 2N NaOH solution, the mixture is heated under reflux for 18 hours. The solvent is distilled off under reduced pressure and the residue is stirred with water. Thus, 5
3.03 g (82% of theory) of-(2,2-dimethylpropionylamino) -4-methoxyimino-3-methylisothiazole are obtained.

A solution of 1.82 g (0.00710 mol) of 5- (2,2-dimethylpropionylamino) -4-methoxyimino-3-methylisothiazole in 1N NaOH solution 2
Heat under reflux in 0 ml and 20 ml of methanol for 1.5 hours. The reaction solution is diluted with water, extracted repeatedly with ethyl acetate, the combined organic phases are dried and concentrated under reduced pressure. The residue is chromatographed on silica gel using cyclohexane / ethyl acetate = 2: 1. Thus, 0.54 of 5-amino-4-methoxyimino-3-methylisothiazole (VIA-2) having a melting point of 118 ° C. to 119 ° C.
g (44% of theory) are obtained.

Use Examples Example A Myzus Test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether 1 part by weight of active compound to produce a suitable formulation of active compound Is mixed with the above amount of the solvent and the above amount of the emulsifier, and the concentrated liquid is diluted with water to a predetermined concentration.

Green peach aphid [green peach aphid (Myzus p.
cabbage (Brassica olera) densely infested with
cea) leaves are treated by dipping in a predetermined concentration of active compound preparation.

After a predetermined period of time, the removal% is determined. 100% means that all aphids have been eliminated, 0% means that none of the aphids have been eliminated.

In this test, at a typical active compound concentration of 0.1%, for example, the following compounds achieved the following control after 6 days: Preparation Examples 3 and 5: 90% Control Preparation Example 4: 95% control Preparation Example 8: 80% control Example B Nephotetix test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound One part by weight of the active compound is mixed with the above-mentioned amount of solvent and the above-mentioned amount of emulsifier, and the concentrated solution is diluted with water to a predetermined concentration.

[0272] Rice (Oryza sativa) seedlings are treated by immersion in a predetermined concentration of the active compound preparation and treated while the seedlings are still wet.
leafhopper (Nephotettix cynticeps)]
To live.

After a predetermined period of time, the removal% is determined. 100% means that all leafhoppers have been destroyed, 0% means that none of the leafhoppers have been destroyed.

In this test, at a typical active compound concentration of 0.1%, for example the compounds of Preparation Examples 3, 4, 5 and 8 achieved 100% control after 6 days.

Example C Larvae test of Phaedon Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, 1 part by weight of the active compound was added as described above. The concentrated solution is mixed with an amount of the solvent and the above-described amount of the emulsifier, and diluted with water to a predetermined concentration.

The leaves of cabbage (Brassica oleracea) are treated by dipping in the active compound preparation at a predetermined concentration and the mustard beetle [mu
larvae of S. beetle (Phaedon cochleariae)].

After a predetermined period of time, the removal% is determined. 100% means that all beetle larvae have been destroyed, 0% means that none of the beetle larvae have been destroyed.

In this test, at a typical active compound concentration of 0.1%, for example the compounds of Preparation Examples 3, 4, 5 and 8 achieved 100% control after 7 days.

Example D Saga (Spodoptera frugiperda) Test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is added in the above amount. And the above-mentioned amount of emulsifier, and the concentrated solution is diluted with water to a predetermined concentration.

The leaves of cabbage (Brassica oleracea) are treated by immersion in a defined concentration of the active compound preparation, and while the leaves are still moist, the oat mot
h (Spodoptera frugiperda)].

After a predetermined period of time, the removal% is determined. 100% means that all larvae have been destroyed, 0% means that none of the larvae have been destroyed.

In this test, at a typical active compound concentration of 0.1%, for example the compounds of Preparation Examples 3, 4, 5 and 8 achieved 100% control after 7 days.

Example E Test Using a Resistant Boophilus microplus / SP-Resistant Parkhurst Variant Test animal: a well-developed female adult Solvent: dimethyl sulfoxide 20 mg of the active compound is dissolved in 1 ml of dimethyl sulfoxide Diluted with the same solvent to a relatively dilute concentration.

The test is repeated five times. 1 μl of the solution is injected into the abdomen and the animals are transferred to dishes and kept in a conditioned room. Determine activity through suppression of spawning. 10
0% means that the ticks did not lay eggs.

In this test, at a typical active compound concentration of 20 μg / animal, for example the compound of Preparation Example 3 achieved 100% control.

Example F Larvae Test / Growth Inhibitory Effect of Flies Fly (Blowfly) Test animal: Larvae of sheep fly (Lucilia cuprina) Solvent: dimethyl sulfoxide 20 mg of the active compound was dissolved in 1 ml of dimethyl sulfoxide and diluted with distilled water. To a relatively dilute concentration.

Approximately 2 in a test tube containing approximately 1 cm ³ of horse meat and 0.5 ml of active compound formulation
0 sheep fly larvae are introduced. After 24 hours and 48 hours, the efficacy of the active compound preparation is determined. Transfer the test tube to a beaker whose bottom is covered with sand. After another two days, the test tubes are removed and the pupae are counted.

The activity of the active compound preparation is assessed by the number of flies that develop 1.5 times after the development period of the untreated control. 100% means that no flies occurred, and 0% means that all flies occurred normally.

In this test, at a typical active compound concentration of 100 ppm, for example, the compound of Preparation Example 3 achieved 100% control.

Example G Cockroach Test Test Animals: Blattella germanica or Periplaneta americana Solvent: dimethyl sulfoxide 20 mg of the active compound is dissolved in 1 ml of dimethyl sulfoxide and diluted with distilled water to obtain Use a dilute concentration.

The 4 test animals are immersed in the active compound preparation to be tested for 1 minute. Transfer the test animals into a plastic beaker and place them in a conditioned room for 7 days,
Decide on extermination.

[0292] 100% means that all cockroaches have been eliminated, 0% means that none of the cockroaches have been eliminated.

In this test, at a typical active compound concentration of 100 ppm, for example, the compound of Preparation Example 3 achieved 100% control.

Example H Plasmopara test (vines) / protection Solvent: acetone 47 parts by weight Emulsifier: alkylaryl polyglycol ether 3 parts by weight To prepare a suitable formulation of the active compound, the active compound 1 The parts by weight are mixed with the above-mentioned amounts of the solvent and the emulsifier, and the concentrated liquid is diluted with water to a predetermined concentration.

To test the protective activity, the active compound preparations are sprayed onto the young seedlings at the specified application rates. After the spray coating has dried, the downy mildew fungus (Plasmopara vi
Seedlings are inoculated with an aqueous spore suspension of ticola) and then placed in a culture cabin at approximately 20 ° C. and 100% relative atmospheric humidity for one day. Thereafter, the seedlings are kept at approximately 21 ° C. for approximately 90
5 days in a greenhouse at atmospheric humidity. The seedlings are then moistened and kept in the hut for one day.

Evaluation is performed 6 days after inoculation. 0% means efficacy equivalent to that of the control, whereas 100% efficacy means that no infection is observed.

In this test, at a typical application rate of 100 g / ha in each case, for example, the compounds of Preparation Examples 3 and 4 are 91% and 100%, respectively.
% Potency.

Example I Sphaerotheca test (cucumber) / protection Solvent: acetone 47 parts by weight Emulsifier: alkylaryl polyglycol ether 3 parts by weight To prepare a suitable formulation of the active compound, 1 part by weight of active compound Is mixed with the above-mentioned amounts of solvent and emulsifier, and the concentrated liquid is diluted with water to a predetermined concentration.

To test the protective activity, young formulations are sprayed with the active compound preparation at the indicated application rates. After the spray coating dries, the powdery mildew fungus (Sphaerothec)
Seedlings are inoculated with an aqueous spore suspension of C. a fulginea). Next, approximately 23 ° C
Put the seedlings in a greenhouse with a relative atmospheric humidity of approximately 70%.

Evaluation is performed 10 days after inoculation. 0% means efficacy comparable to that of the control, whereas 100% efficacy means that no infection is observed.

In this test, for example, the compound of Preparation Example 7 showed an efficacy of 97% at a typical application rate of 100 g / ha in each case.

Example J Uncinula test (vine) / Protective Solvent: acetone 47 parts by weight Emulsifier: alkylaryl polyglycol ether 3 parts by weight To prepare a suitable formulation of the active compound, the active compound 1 The parts by weight are mixed with the above amounts of the solvent and the emulsifier, and the concentrated liquid is diluted with water to a predetermined concentration.

To test the protective activity, the active compound preparations are sprayed on the young seedlings at the specified application rates. After the spray coating dries, the grape powdery mildew (Uncinula)
The seedlings are inoculated with an aqueous spore suspension of the spores. It is then placed in a greenhouse at approximately 23 ° C. and a relative atmospheric humidity of approximately 70%.

Evaluation is performed 14 days after the inoculation. 0% means efficacy equivalent to that of the control, whereas 100% efficacy means that no infection is observed.

In this test, at a typical application rate of 100 g / ha, for example, each of the compounds of Preparation Examples 3 and 7 showed 100% efficacy.

Example K Venturia Test (Apple) / Protective Solvent: Acetone 47 parts by weight Emulsifier: Alkylaryl polyglycol ether 3 parts by weight To prepare a suitable formulation of the active compound, 1 part by weight of active compound Is mixed with the above-mentioned amounts of solvent and emulsifier, and the concentrated liquid is diluted with water to a predetermined concentration.

In order to test the protective activity, the active compound preparations are sprayed on the young seedlings at the specified application rates. After the spray coating has dried on, the seedlings are inoculated with an aqueous suspension of conidia of the scab (Venturia inaequalis), the organism responsible for apple rot, and then at about 20 ° C. and 100% relative atmospheric humidity. For 1 day.

Next, the seedlings are placed in a greenhouse at approximately 21 ° C. and a relative atmospheric humidity of approximately 90%.

Evaluation is performed 12 days after inoculation. 0% means efficacy equivalent to that of the control, whereas 100% efficacy means that no infection is observed.

In this test, at a typical application rate of 100 g / ha, for example the compound of Preparation Example 7 showed an efficacy of 100%.

──────────────────────────────────────────────────続 き Continuation of front page (81) Designated country EP (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE ), OA (BF, BJ, CF, CG, CI, CM, GA, GN, GW, ML, MR, NE, SN, TD, TG), AP (GH, GM, KE, LS, MW, SD, SZ, UG, ZW), EA (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, CA, CH, CN, CU, CZ, DE, DK, EE, ES, FI, GB, GE, GH, GM, HR, HU, ID, IL, IS, JP, KE, KG, KP , KR, KZ, LC, LK, LR, LS, LT, LU, LV, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, UA, UG, US, UZ, VN, YU, ZW (72) Inventor Krefeld, Gerd D-41468 Neus-Franziscus-Coussieu, Germany Trasse 27 (72) Inventor Erderen, Christophe Federal Republic of Germany-42799 Reichlingen Unterbilscherhof 15 (72) Inventor Schuttenzel, Krauss Federal Republic of Germany Day-40595 Deutzell Dorf Seesenasi Jutrase 17 (72) Inventor Türberg, Andreas, Federal Republic of Germany-42781 Hahn Ginterschüterse 86 (72) Inventor Menke, Norbert of Federal Republic of Germany -51,381 Refueru Kuzen Gurung del Mi Yu-les-2 F-term (reference) 4C033 AA04 AA05 AA06 AA07 AA08 AA16 AA17 4H011 AA01 AA03 AC01 AC02 AC03 AC04 AC08 AE01 BA01 BB05 BB13 BC03 BC06 BC07 DA16 DE15

Claims (11)

[Claims] 1. A compound of the formula (I) Wherein R ¹ represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, alkylamino, dialkylamino or optionally substituted cycloalkyl; R ² represents hydrogen, halogen, cyano, nitro , Thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, halogenoalkylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl, thiocarbamoyl, alkoxy, formyl, alkylcarbonyl or CR ⁷ -NOR ⁸ (here in, each of R ⁷ and R ^8, independently of one another hydrogen, alkyl, halogenoalkyl, alkenyl, cycloalkyl or Shikuroa optionally substituted respectively Or represents Kiruarukiru, or represents represents.) Was substituted aryl or arylalkyl optionally each, R ³ is alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, alkynyl, alkylcarbonyloxy, alkoxycarbonyl oxy Alkyl; each represents optionally substituted aryl, arylalkyl or aryloxyalkyl; each represents optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl or cycloalkylthioalkyl, or -N = CR ⁵ R ⁶ (where
Each of R ⁵ and R ⁶ independently of one another represents hydrogen, alkyl, halogenoalkyl, alkenyl, each optionally substituted cycloalkyl or cycloalkylalkyl, or each optionally substituted aryl or arylalkyl Or R ⁵ and R ⁶ together with the carbon atom to which they are attached, represent an optionally substituted carbocyclic ring. R ⁴ represents an optionally substituted aryl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, or an optionally substituted heterocycle; A represents oxygen or sulfur Y represents optionally substituted alkylene, alkenylene or alkyleneoxy, respectively, and Z represents oxygen or sulfur. ] The compound of these. 2. R¹ Is C₁ -C_Four Alkyl, 1 to 5 identical or different
Having a halogen atom (eg, a fluorine, chlorine or bromine atom)₁ -C_Four Halogeno
Alkyl, C₁ -C_Four Alkoxy-C₁ -C_Four Alkyl, C₁ -C_Four Alkyl
O-C₁ -C_Four Alkyl, C₁ -C_Four Alkoxy, C₁ -C_Four Alkylthio, C ₁ -C_Four Alkylamino, di (C₁ -C_Four Alkyl) amino or C₁ 
-C_Four Alkyl or halogen (eg, fluorine, chlorine or bromine) from the group consisting of
Optionally mono- or tri-substituted C with one or different substituents_Three -C₆ Cycloal
Represents a kill; R^Two Is hydrogen, halogen, cyano, nitro, thiocyanato, C₁ -C_Four Alkoki
Cicarbonyl, C_Two -C_Four Alkenyloxycarbonyl, C₁ -C_Four Alkyl
E. 1 to 5 identical or different halogen atoms (eg fluorine or chlorine atom)
Having C₁ -C_Four Halogenoalkylthio, C₁ -C_Four Alkylsulfinyl, 1
Having from 5 to 5 identical or different halogen atoms (eg fluorine or chlorine atoms)
C₁ -C_Four Halogenoalkylsulfinyl, C₁ -C_Four Alkylsulfonyl, 1
Having from 5 to 5 identical or different halogen atoms (eg fluorine or chlorine atoms)
C₁ -C_Four Halogenoalkylsulfonyl, thiocarbamoyl, C₁ -C_Four Arco
Kishi, formyl, C₁ -C_Four Represents alkylcarbonyl, or -CR⁷ = NO
R⁸ And R⁷ And R⁸ Are each independently of the other hydrogen, C₁ -C_Four Alkyl, one
C containing up to 5 identical or different halogen atoms (eg fluorine or chlorine atoms)₁ 
-C_Four Halogenoalkyl, C_Two -C_Four Represents alkenyl; C₁ -C_Four Alkyl
The same or different substitutions from the group consisting of and halogens (eg fluorine, chlorine or bromine)
Optionally monosubstituted or trisubstituted C_Three -C₆ Cycloalkyl or
C_Three -C₆ Cycloalkyl-C₁ -C_Four Represents alkyl; or the same or different
Phenyl or phenyl-C, each optionally substituted with mono- or tri-substituted substituents ₁ -C_Four Alkyl, in which case the possible substituents on the phenyl ring are
If halogen, nitro, cyano, C₁-C_FourAlkyl, 1 to 5 identical or
C with different halogen atoms (eg fluorine or chlorine atoms)₁ -C_Two Halogenoa
Luquil, C₁ -C_Four Alkoxy, C₁ -C_Four Alkylthio, 1 in each case
Having from 5 to 5 identical or different halogen atoms (eg fluorine or chlorine atoms)
C₁ -C_Two Halogenoalkoxy and C₁ -C_Two Halogenoalkylthio, C₁ -C _Four Alkoxycarbonyl and C₁ -C_Four Alkylcarbonyloxy, R^Three Is C₁ -C₈ Alkyl, 1 to 5 identical or different halogen atoms (eg,
C having, for example, a fluorine or chlorine atom)₁ -C_Four Halogenoalkyl, C₁ -C_Four Al
Koxy-C₁ -C_Four Alkyl, C₁ -C_Four Alkylthio-C₁ -C_Four Alkyl,
C_Two -C_Four Alkenyl, C_Two -C_Four Alkynyl, C₁ -C_Four Alkylcarbonyl
Oxy-C₁ -C_Four Alkyl, C₁ -C_Four Alkoxycarbonyloxy-C₁ −
C_Four Represents alkyl; phenyl, phenyl-C₁ -C_Four Alkyl or phenoxy
C₁ -C_Four Alkyl [each of which is the same or different
Is optionally mono- or tri-substituted, and possible substituents are halogen, nitro
, Cyano, C₁ -C_Four Alkyl, 1 to 5 identical or different halogen atoms (
C having, for example, a fluorine or chlorine atom)₁ -C_Two Halogenoalkyl, C₁ -C_Four A
Lucoxy, C₁ -C_Four Alkylthio, in each case 1 to 5 identical or
C with different halogen atoms (eg fluorine or chlorine atoms)₁ -C_Two Halogenoa
Lucoxy and C₁ -C_Two Halogenoalkylthio, C₁ -C_Four Alkoxycarboni
And C₁ -C_Four Alkylcarbonyloxy. ] Or C₁ -C_Four The group consisting of alkyl and halogen (eg fluorine, chlorine or bromine)
Optionally mono- or tri-substituted C with the same or different substituents from_Three 
-C₆ Cycloalkyl, C_Three -C₆ Cycloalkyl-C₁ -C_Four Alkyl, C_Three 
-C₆ Cycloalkoxy-C₁ -C_Four Alkyl or C_Three -C₆ Cycloalkyl
O-C₁ -C_Four Represents alkyl, or -N = CR^Five R⁶ And R^Five And R⁶ Are each independently of the other hydrogen, C₁ -C_Four Alkyl, one
C containing up to 5 identical or different halogen atoms (eg fluorine or chlorine atoms)₁ 
-C_Four Halogenoalkyl, C_Two -C_Four Represents alkenyl; C₁ -C_Four Alkyl
The same or different substitutions from the group consisting of and halogens (eg fluorine, chlorine or bromine)
Optionally monosubstituted or trisubstituted C_Three -C₆ Cycloalkyl or
C_Three -C₆ Cycloalkyl-C₁ -C_Four Represents alkyl; or phenyl or
Is phenyl-C₁ -C_Four Alkyl [each of which may be the same or different
Is optionally mono- or tri-substituted and the possible substituents on the phenyl ring are
In each case halogen, nitro, cyano, C₁ -C_Four Alkyl, 1 to 5
Having the same or different halogen atoms (eg fluorine or chlorine atoms)₁ -C_Two 
Halogenoalkyl, C₁ -C_Four Alkoxy, C₁ -C_Four Alkylthio, each
1 to 5 identical or different halogen atoms (eg fluorine and chlorine atoms)
C)₁ -C_Two Halogenoalkoxy and C₁ -C_Two Halogenoalkylthio
, C₁ -C_Four Alkoxycarbonyl and C₁ -C_Four With alkylcarbonyloxy
is there. Or R^Five And R⁶ Is, together with the carbon atom to which it is attached, C₁ -C_Four Alkyl,
C₁ -C_Four The group consisting of alkoxy and halogen (eg fluorine, chlorine or bromine)
5- or 7-membered mono- or tri-substituted optionally with the same or different substituents
R represents a carbocyclic ring;^Four Is C_Three -C₈ Cycloalkyl or C_Four -C₈ Cycloalkenyl (these
Each is optionally mono- or polysubstituted with the same or different substituents,
Possible substituents are halogen, C₁ -C_Four Alkyl, C₁ -C_Four Alkoxy, C₁ 
-C_Four Halogenoalkyl, C₁ -C_Four Halogenoalkoxy, hydroxyl and C ₁ -C_Four Alkylcarbonyl. ) Or phenyl [wherein the phenyl is optionally mono- or
It is penta-substituted (preferably mono- to tri-substituted) and possible substituents are halogen
, Nitro, cyano, C₁ -C_Four Alkyl, C₁ -C_Four Alkoxy, C₁ -C_Four A
Lucircio, C₁ -C_Four Halogenoalkyl, C₁ -C_Four Halogenoalkoxy, C ₁ -C_Four Halogenoalkylthio, hydroxyl-C₁ -C_Four Alkyl, C₁ -C _Four Alkylcarbonyl, C₁ -C_Four Alkoxycarbonyl, C₁ -C_Four Alkyl
Carbonyloxy, amino, C₁ -C_Four Alkylamino, C₁ -C_Four Alkylka
Rubonylamino, di (C₁ -C_Four ) Alkylamino, C_Two -C₆ Alkenyloxy
Si, C_Two -C₆ Halogenoalkenyloxy, identical or different halogen substituents
Optionally mono- or polysubstituted C_Four -C₆ Cycloalkenyloxy; and
Nil, phenoxy, phenylthio, benzyl, pyridinyloxy, pyrimidinyl
Oxy, thiazolyloxy or thiadiazolyloxy (each of which is
Optionally mono- or tri-substituted with one or different substituents, possible substituents are
, Halogen, nitro, cyano, C₁ -C_Four Alkyl, C₁ -C_Four Alkoxy, C ₁ -C_Four Alkylthio, C₁ -C_Four Alkylsulfinyl, C₁ -C_Four Alkyl
Sulfonyl, C₁ -C_Four Alkylcarbonyl, aminothiocarbonyl, aminoca
Rubonil, C₁ -C_Four Alkoxyimino-C₁ -C_Four Alkyl, C₁ -C_Four Halo
Genoalkyl, C₁ -C_Four Halogenoalkoxy and C₁ -C_Four Halogenoalkyl
Thio. ). Or a 5- or 6-membered heterocyclic ring, which may be the same or different and
Mono- to tri-substituted and one to three of N, S and O atoms, etc.
Having a heteroatom and may contain a CO group as a ring member,
Substituents are halogen, nitro, cyano, C₁ -C_Four Alkyl, C₁ -C_Four Arco
Kissi, C₁ -C_Four Alkylthio, C₁ -C_Four Halogenoalkyl, C₁ -C_Four Halo
Genoalkoxy, C₁ -C_Four Halogenoalkylthio, phenylsulfonyl (this
Is C₁ -C_Four Alkyl, halogen, C₁ -C_Four Halogenoalkyl, C₁ -C_Four 
Alkoxy and C₁ -C_Four Same or different from the group consisting of halogenoalkoxy
It is optionally mono- or disubstituted with substituents. ) And phenyl, phenoxy
, Phenylthio or benzyl (each of which is the same or different
Where possible, they are mono- or tri-substituted, and possible substituents are halogen, nitro,
Ano, C₁ -C_Four Alkyl, C₁ -C_Four Alkoxy, C₁ -C_Four Alkylthio,
C₁ -C_Four Halogenoalkyl, C₁ -C_Four Halogenoalkoxy and C₁ -C_Four C
Logenoalkylthio. ). A represents oxygen or sulfur, Y represents C₁ -C₆ Alkylene, C₁ -C₆ Hydroxyalkylene, C₁ -C_Four A
Lucoxy-C₁ -C₆ Alkylene, C₁ -C_Four Alkylcarbonyloxy-C₁ 
-C₆ Alkylene, cyano-C₁ -C₆ Alkylene, 1 to 5 identical or different
Having a halogen atom (eg, a fluorine or chlorine atom)₁ -C_Four Halogenoal
Alkylene; with the same or different substituents from the group consisting of fluorine, chlorine and methyl
Each mono- or tri-substituted C_Three -C₆ Cycloalkyl-C₁ -C_Four A
Lucylene, C_Two -C_Four Alkenylene or C₁ -C_Four Represents alkenyleneoxy,
The compound of formula (I) according to claim 1, wherein Z represents oxygen or sulfur. 3. R¹ Is methyl, ethyl, n- or i-propyl, n-, i
-, S- or t-butyl; CH_Two F, CHF_Two , CF_Three , CH_Two Cl, CH_Two B
r, CHClCH_Three Methoxy, ethoxy, methylthio, methylamino, methoxy
Cimethyl, ethoxymethyl; represents methylthiomethyl or cyclopropyl;^Two Is hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; methoxycarbonyl
, Ethoxycarbonyl, i-propoxycarbonyl, n-propoxycarbonyl
Allyloxycarbonyl; CSNH_Two , SCH_Three , SOCH_Three , SO_Two CH _Three , CHO, COCH_Three , CH = NOCH_Three Or C (CH_Three ) = NOCH_Three The table
Then R^Three Is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
Chill, n-pentyl, n-hexyl, n-heptyl, n-octyl; 1 to 5
C containing two identical or different halogen atoms (eg fluorine or chlorine atoms)₁ -C _Two Halogenoalkyl, C₁ -C_Two Alkoxy-C₁ -C_Two Alkyl, C₁ -C_Two 
Alkylthio-C₁ -C_Two Alkyl, C_Two -C_Four Alkenyl, C_Two -C_Four Archi
Nil, C₁ -C_Two Alkylcarbonyloxy-C₁ -C_Two Alkyl, C₁ -C_Two 
Alkoxycarbonyloxy-C₁ -C_Two Represents alkyl; or phenyl, phenyl-C₁ -C_Two Alkyl or phenoxy-C₁ -C_Two Al
Kill (each of which is optionally substituted on the phenyl ring with the same or different substituents)
Substituted or trisubstituted, the possible substituents are fluorine, chlorine, bromine, nitro,
No, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylthio,
Trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxy
It is cicarbonyl or methylcarbonyloxy. ) Or cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl
, Cyclopentylmethyl or cyclohexylmethyl (each of these
The monoalkyl or tri-substituted alkyl group is the same or different, and
Possible substituents are methyl, ethyl, n- or i-propyl, fluorine, chlorine and odor.
Is prime. ) Or -N = CR^Five R⁶ And R^Five And R⁶ Are each independently of the other methyl, ethyl, n- or i-pro
Represents pill, n-, i-, s- or t-butyl; or phenyl or phenyl
Le-C₁ -C_Two Alkyl (each of which has the same or different positions on the phenyl ring)
The substituents are optionally mono- or tri-substituted, with possible substituents being fluorine, chlorine, odor
Element, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy
Si, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl or methyl
Carbonyloxy. ) Or R^Five And R⁶ Is, together with the carbon atom to which it is attached, methyl, ethyl, meth
Optionally monosubstituted with the same or different substituents from the group consisting of xyl, fluorine and chlorine
Or a disubstituted 6-membered carbocyclic ring;^Four Is cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexene
Nil, each of which is optionally substituted with the same or different substituents,
(Preferably mono- or di-substituted), possible substituents are fluorine, chlorine,
Bromine, methyl, ethyl, isopropyl, methoxy, trifluoromethyl and methyl
Carbonyl. Or phenyl, where phenyl is the same or different and is optionally mono- or tri-substituted.
Substituted and possible substituents are fluorine, chlorine, nitro, cyano; methyl, ethyl
, N- or i-propyl, n-, i-, s- or t-butyl;
Xy, n- or i-propoxy; methylthio; -CF_Three -CHF_Two , -CH_Two C
F_Three , -CH_Two -CF_Two -CHF_Two , -CH (CF_Three ) -CH_Three ; -OCF_Three ,
-OCHF_Two , -OCH_Two CF_Three , -O-CH_Two -CF_Two -CF_Three , -OCH_Two 
-CF_Two -CHF_Two , -O-CH (CF_Three ) -CH_Three ; -SCF_Three ; -CH_Two O
H: methylcarbonyl, ethylcarbonyl; methoxycarbonyl, ethoxycal
Bonyl; methylcarbonyloxy, ethylcarbonyloxy; amino, methyla
Mino, dimethylamino, methylcarbonylamino;And phenyl, phenoxy or phenylthio, each of which is the same or
Mono- or di-substituted, optionally with different substituents, possible substituents are fluorine
, Chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio,
Trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methyl
Sulfinyl, methylsulfonyl, methylcarbonyl, aminothiocarbonyl
is there. ). Or the following heterocycle:[Each of which is optionally mono- or disubstituted with the same or different substituents;
And possible substituents are fluorine, chlorine, nitro, cyano; methyl, ethyl, n
-Or i-propyl, n-, i-, s- or t-butyl; methoxy, ethoxy,
n- or i-propoxy; methylthio; -CF_Three , -CHF_Two , -CH_Two CF_Three 
, -CH_Two CHF_Two , -CH (CF_Three ) -CH_Three ; -OCF_Three , -OCHF_Two ,
-OCH_Two CF_Three , -O-CH_Two -CF_Two -CF_Three , -OCH_Two -CF_Two -CH
F_Two , -O-CH (CF_Three ) -CH_Three ; -SCF_Three ; And phenyl, phenoxy
Or phenylthio, each of which is optionally substituted with the same or different substituents
Substituted or disubstituted, possible substituents are fluorine, chlorine, nitro, cyano,
Chill, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trif
Fluoromethoxy and trifluoromethylthio. ); Where R⁹ Is C₁ -C_Four Alkyl, especially methyl or ethyl; C₁ -C _Four Alkylcarbonyl, for example especially methylcarbonyl or ethylcarbonyl
Or phenylsulfonyl (the phenylsulfonyl is C₁ -C_Four Archi
Halogen, such as especially fluorine or chlorine; C₁ −
C_Four Halogenoalkyl, such as especially trifluoromethyl; C₁ -C_Four Alkoxy
And especially methoxy; and C₁ -C_Four Halogenoalkoxy, such as especially trif
Optionally monosubstituted with the same or different substituents from the group consisting of fluoromethoxy or
Disubstituted. ). A represents oxygen or sulfur; Y represents a group —CH_Two -, -CH (CH_Three )-, -CH (C_Two H_Five )-, -CH (n
-C_Three H₇ )-, -CH (i-C_Three H₇ )-, -CH_Two CH_Two -, -CH (OH
)-, -CH (OCH_Three )-, -CH (O-CO-CH_Three )-, -CH (CN)
-, -CHF-, -CHCl-,-CH = CH- or -CH_Two The compound of formula (I) according to claim 1, wherein one of O- is represented and Z represents oxygen or sulfur. 4. R ¹ is methyl, ethyl, n- or i-propyl, n-, i-
, S- or t- _{butyl; CH 2 F, CHF 2,} CF 3, CH 2 Cl, CH 2 Br
Represents methoxy, ethoxy, methylthio, methylamino or cyclopropyl;
R ² is hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, CSNH ₂ , SCH ₃ , SOCH ₃ , SO ₂ CH ₃ , CHO, COC
H _3, CH = NOCH ₃ or C (CH ₃₎ = represents NOCH _3, R ³ is methyl, ethyl, n- or i- propyl, n-, i-, s- or t- butyl; chloroethyl; 2 Methoxymethyl, methoxyethyl; allyl, propargyl; phenyl or benzyl, each of which is optionally mono- or disubstituted on the phenyl ring with the same or different substituents; Possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl or methylcarbonyloxy), or Cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl
(Each of which represents a cycloalkyl moiety optionally mono- or di-substituted with the same or different substituents from the group consisting of methyl, fluorine and chlorine), or -N = CR ⁵ R ⁶ Wherein each of R ⁵ and R ⁶ independently of one another represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; or phenyl or benzyl
(In each of these, the phenyl ring is optionally mono- or disubstituted with the same or different substituents, and possible substituents include fluorine, chlorine, bromine, nitro, cyano,
Methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl and methylcarbonyloxy. R ⁴ is phenyl [this phenyl is optionally mono- or tri-substituted (preferably mono- or di-substituted), and possible substituents are methoxy, ethoxy, i-propoxy; _{3, -OCHF 2, -OCH 2 CF} 3, -OCH 2 CF 2 C
_{F 3, -OCH 2 CF 2 CHF} 2, -OCH (CF 3) -CH 3 and fluorine, optionally, chlorine, trifluoromethyl, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, amino thiocarbonyl, nitro or cyano Is a phenoxy substituted with Or a heterocyclic ring represented by the following formula: [Each of which methoxy, _{ethoxy, -OCF 3, -OCH 2 CF 3} ,
-OCH ₂ CF ₂ CF _3, optionally substituted or optionally substituted with -OCH (CF ₃₎ -CH _3, or optionally fluorine, chlorine, phenoxy substituted with nitro or cyano. Represents one of the]; A represents oxygen, Y is _{-CH 2, -CH (CH 3)} -, - CH (OCH 3) - or -CH (OCO
The compound of formula (I) according to claim 1, wherein CH ₃ ) — represents Z. 5. a) Formula (II): [Wherein each of R ¹ , R ² , R ⁴ and Y is the same as defined in claim 1]. A compound of formula (III) R ³ -A-CZ-G (III) wherein each of R ³ , A and Z is the same as defined in claim 1,
And G represents a leaving group. Or b) reacting with a compound of formula (IV) Wherein ^each of R ¹ , R ² , R ³ , A and Z is the same as defined above.
] In the formula (V) R ⁴ -Y-CO-G (V) wherein R ⁴ , Y and G are the same as defined above. A process for the preparation of compounds of the formula (I), characterized in that they are carried out in each case in the presence of a base and, if appropriate, in the presence of a diluent. 6. A compound of the formula (IV) [Wherein ^each of R ¹ , R ² , R ³ , A and Z is the same as defined in claim 1]. ] The compound of these. 7. A compound of the formula (VI A)中 where R¹ Is the same as defined in claim 1, and R^2-1 Is R, -CO-R^7-1 Or -CR^7-1 = NOR⁸ Wherein R is alkylthio, halogenoalkylthio, alkylsulfinyl, halogeno
Alkylsulfinyl, alkylsulfonyl and halogenoalkylsulfonyl
Represents, R^7-1 Represents hydrogen or alkyl;⁸ Is hydrogen, C₁ -C_Four Alkyl, 1 to 5 identical or different halogen atoms
C having an atom (for example, a fluorine or chlorine atom)₁ -C_Four Halogenoalkyl, C_Two -C _Four Represents alkenyl; C_Three -C₆ Cycloalkyl or C_Three -C₆ Cycloalkyl
-C₁ -C_Four Alkyl (each of which is a C₁ -C_Four Alkyl and halogen
Optionally mono- or tri-substituted with the same or different substituents from the group consisting of
You. ) Or phenyl or phenyl-C₁ -C_Four Alkyl [these
Are optionally mono- or tri-substituted with the same or different substituents.
, Possible substituents on the phenyl ring are, in each case, halogen, nitro, cyano
No, C₁ -C_Four Alkyl, 1 to 5 identical or different halogen atoms (eg,
C having fluorine and chlorine atoms)₁ -C_Two Halogenoalkyl, C₁ -C_Four Alkoki
Si, C₁ -C_Four Alkylthio, in each case 1 to 5 identical or different
C containing halogen atoms (eg, fluorine and chlorine atoms)₁ -C_Two Halogenoalkoki
Si and C₁ -C_Two Halogenoalkylthio, C₁ -C_Four Alkoxycarbonyl and
C₁ -C_Four Alkylcarbonyloxy. ].化合物 Compound. 8. A pesticidal and fungicidal agent comprising the compound of the formula (I) according to claim 1. 9. Use of a compound of formula (I) according to claim 1 for controlling pests and fungi. 10. Control of pests, fungi and molds, wherein the compound of the formula (I) according to claim 1 is allowed to act on pests, fungi and molds and / or their habitats. Method. 11. A process for producing a pesticide and a fungicide, which comprises mixing the compound of formula (I) according to claim 1 with a bulking agent and / or a surfactant.