CN1232464A - Substd. N-isothiazolyl-(thio) amides - Google Patents

Substd. N-isothiazolyl-(thio) amides Download PDF

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CN1232464A
CN1232464A CN97198430A CN97198430A CN1232464A CN 1232464 A CN1232464 A CN 1232464A CN 97198430 A CN97198430 A CN 97198430A CN 97198430 A CN97198430 A CN 97198430A CN 1232464 A CN1232464 A CN 1232464A
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M·海尔
T·布雷特施奈德
G·克雷菲尔德
C·埃尔德伦
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Abstract

New N-isothiazolyl-(thio)amides have the formula (I), in which Q stands for the grouping (a), in which Het stands for an optionally substituted heterocycle, and R, X, Y and A have the meanings given in the description. Also disclosed are several processes for preparing the same and their use for controlling animal pests.

Description

N-isothiazolyl-(sulphur) acid amides that replaces
The present invention relates to new N-isothiazolyl-(sulphur) acid amides, its multiple preparation method, with and the control animal pest purposes.
More known N-isothiazolyl amide derivatives have insecticidal properties (referring to, for example EP-A-0623282 and WO-A95/31448).
But, the drug effect of these prior art compound effects and/or medicine phase, particularly kill certain micro-organisms or when low application concentration, always be not entirely satisfactory in all use fields.
Therefore, the invention provides N-isothiazolyl-(sulphur) acid amides of the new replacement of formula I Wherein Q represents group
Figure A9719843000152
Wherein substituted heterocycle is chosen in the Het representative wantonly; R represents hydrogen; alkyl; haloalkyl; alkoxyalkyl, alkyl-carbonyl, alkyl sulphonyl; optional separately substituted aryl carbonyl; aryl sulfonyl or arylalkyl, perhaps substituted cycloalkyl is chosen in representative wantonly, and X represents oxygen or sulphur; the optional substituted alkylidene group of Y representative; alkylene group, alkylidene group oxygen base or alkylidene group sulfenyl and the optional substituted aryl of A representative; optional substituted cycloalkyl, optional substituted cycloalkenyl or optional substituted heterocycle.
Find in addition, a) in the presence of alkali and in the presence of thinner, when the acyl halide of the aminoisothiazoles of formula II and formula III reacts, obtain the formula (N-isothiazolyl-acid amides of I replacement a) Q wherein, R, Y and A be as above definition separately,
Figure A9719843000162
Wherein Q and R as above definition separately,
Hal-CO-Y-A (III) is Y and A as above definition separately wherein, represent halogen with Hal, and b) if suitably in the presence of thinner, when the formula that is obtained by method (a) (when I N-isothiazolyl-acid amides a) and sulfuration reagent react, obtains the N-isothiazolyl-thioamides of the replacement of formula (I b)
Figure A9719843000163
Q wherein, R, Y and A be as above definition separately,
Figure A9719843000171
Q wherein, R, Y and A be as above definition separately; And c), when the dithioesters reaction of the aminoisothiazoles of formula II and formula IV, also obtains the N-isothiazolyl-thioamides of the replacement of formula (I b) if suitably in the presence of thinner
Figure A9719843000172
Q wherein, R, Y and A be as above definition separately,
Figure A9719843000173
Wherein Q and R as above definition separately, Wherein as above definition and Alk represent alkyl or group MO-CO-CH separately for Y and A 2-, wherein M represents basic metal (for example sodium or potassium).
Find that in addition the N-isothiazolyl of the replacement that formula I is new-(sulphur) acid amides is fit to control animal pest, particularly agricultural, forestry, the insect that storing products and material protection and health field ran into, Arachnida and nematode very much.
Describe in detail above below and the preferred substituents and/or the scope of group shown in the structural formula of hereinafter mentioning: Q preferably represents group
Figure A9719843000181
Wherein Het representative has 1 or 2 heteroatoms, N for example, S and O atom, optional by identical or different substituting group one to trisubstituted 5-or 6-unit heterocycle, possible substituting group is a halogen, C 1-C 4-alkyl, C 1-C 4-alkoxyl group has for example fluorine of 1-5 identical or different halogen atom, the C of chlorine and bromine atoms 1-C 4-haloalkyl, C 1-C 4-alkoxy-C 1-C 4-alkyl, nitro, C 1-C 4-alkyl-alkylsulfonyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkyl sulfonyl, and thiocarbamoyl.R preferably represents hydrogen, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxy-C 1-C 4-alkyl, C 1-C 4-alkyl-carbonyl, C 1-C 4-alkyl-alkylsulfonyl is represented phenylcarbonyl group, phenyl-alkylsulfonyl or benzyl, and it is chosen wantonly on benzyl ring separately by one to three replacement of identical or different substituting group, and possible substituting group is halogen in all cases, nitro, cyano group, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 2-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 2-halogenated alkoxy, or have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 2-halogenated alkylthio, perhaps representative is optional by the identical or different C that is selected from 1-C 4The substituting group one of-alkyl and halogen is to trisubstituted C 3-C 6-cycloalkyl.X preferably represents oxygen or sulphur.Y preferably represents C 1-C 6-alkylidene group, C 1-C 6-hydroxy alkylidene, C 1-C 4-alkoxy-C 1-C 6-alkylidene group, C 1-C 4-alkyl-carbonyl oxygen base-C 1-C 6-alkylidene group, cyano group-C 1-C 6-alkylidene group has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halo alkylidene group; Optional by the identical or different fluorine that is selected from, the substituting group one of chlorine and methyl is to trisubstituted C 3-C 6-cycloalkyl-C 1-C 4-alkylidene group, C 2-C 4-alkylene group, C 1-C 4-alkylidene group oxygen base or C 1-C 4-alkylidene group sulfenyl.A preferably
(1) representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is: halogen, nitro, cyano group, C 1-C 12-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 12-haloalkyl, C 1-C 12-alkoxyl group has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 12-halogenated alkoxy, C 1-C 12-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 12-halogenated alkylthio, C 2-C 12-alkenyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 12-halogenated alkenyl, optional by the identical or different C that is selected from 1-C 4The substituting group one of-alkyl and halogen is to trisubstituted C 3-C 8-cycloalkyl, following group
Figure A9719843000191
And phenyl, phenoxy group, thiophenyl, benzyl, benzyl oxygen base; pyridyl oxygen base, pyrimidyl oxygen base, pyrazinyl oxygen base or pyridazinyl oxygen base, these groups are optional separately to be selected from one to three replacement of following group by identical or different: halogen; nitro, cyano group, thiocarbamoyl, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkoxy-C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 1-C 4-alkylthio-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphonyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl, C 1-C 4-alkyl sulphonyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkyl sulfonyl, formyl radical, C 1-C 4-alkyl-carbonyl, C 1-C 4-alkoxy carbonyl, C 1-C 4-alkoxyl group imido grpup-C 1-C 4-alkyl, optional by C 1-C 4One of-alkyl-replacement De oxadiazole base and following group
Figure A9719843000201
(2) the optional C that is replaced by identical or different substituting group one to five of representative 5-C 8-cycloalkenyl or C 3-C 8-cycloalkyl, possible substituting group is C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 3-C 8-cycloalkyl, and optional by the identical or different halogen that is selected from, nitro, cyano group, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group and have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4The substituting group one of-halogenated alkoxy is to trisubstd phenyl;
(3) representative has a 1-3 heteroatoms, N for example, S and O atom, can randomly also contain one or more CO and/or CS group for becoming ring members, and optional by identical or different substituting group one to trisubstituted 5-or 6-unit heterocycle, possible substituting group is: halogen, nitro, cyano group, C 1-C 4-alkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, perhaps phenyl, phenoxy group, thiophenyl or benzyl, these groups are optional separately to be replaced by identical or different substituting group one to three, and possible substituting group is: halogen, nitro, cyano group, C 1-C 4-alkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy and have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio; And the N-H group that wherein randomly is present in replacement hydrogen atom in the heterocycle can be by C 1-C 6-alkyl, C 1-C 6-alkyl-carbonyl or phenyl sulfonyl replace, and this substituting group again can be randomly by C 1-C 6-alkyl, halogen has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group or have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy replaces; Perhaps
(4) representative also contains one or more heteroatomss, N for example, S or O atom, perhaps one or more CO groups are for becoming ring members, and the optional condensed two that is replaced by identical or different substituting group one to five-or three cyclic groups, possible substituting group is: halogen, nitro, cyano group, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxy-C 1-C 4-alkyl, C 1-C 4-alkoxyl group has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 1-C 4-alkyl sulphinyl, C 1-C 4-alkyl sulphonyl, hydroxyl, sulfydryl, C 1-C 4-alkyl-carbonyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkyl carbonyl, C 1-C 4-carbalkoxy or phenyl, phenoxy group, thiophenyl or benzyl, these groups are optional separately to be replaced by identical or different substituting group one to three, and particularly at phenyl moiety, possible substituting group is: halogen, nitro, cyano group, C 1-C 4-alkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy and have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio; R wherein 1Represent hydrogen, C 1-C 8-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, representative is optional by identical or different halogen and the C of being selected from 1-C 4The substituting group one of-alkyl or polysubstituted C 3-C 7-cycloalkyl, perhaps representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a halogen, C 1-C 4-alkyl or C 1-C 4-alkoxyl group, R 2And R 3Be identical or different, represent hydrogen or C separately 1-C 4-alkyl; R 4Represent C 1-C 8-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, representative is optional by identical or different halogen and the C of being selected from 1-C 4The substituting group one of-alkyl or polysubstituted C 3-C 7-cycloalkyl, perhaps representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a halogen, C 1-C 4-alkyl or G 1-C 4-alkoxyl group; Represent oxygen or group=N-OR with W 5With=N-NR 6R 7One of, R wherein 5Represent C 1-C 6-alkyl or representative are optional by the identical or different halogen that is selected from, nitro, cyano group, thiocarbamoyl, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkoxy-C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 1-C 4-alkylthio-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphonyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl, C 1-C 4-alkyl sulphonyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkyl sulfonyl, formyl radical, C 1-C 4-alkyl-carbonyl, C 1-C 4-alkoxy carbonyl and C 1-C 4-alkoxyl group imido grpup-C 1-C 4The substituting group one of-alkyl is to trisubstituted benzyl; And R 6And R 7Be identical or different, represent hydrogen, C separately 1-C 6-alkyl or representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a halogen, nitro, cyano group, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group or have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy.One of group below Q especially preferably represents Z wherein 1, Z 2And Z 3Be identical or different, represent hydrogen separately, chlorine, bromine, nitro, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or tert-butyl; CH 2F, CHF 2, CF 3, CH 2Cl, CH 2Br, CHClCH 3Methoxyl group, oxyethyl group, methoxymethyl or ethoxyl methyl.R especially preferably represents hydrogen, methyl, and ethyl, just-or different-propyl group; Methoxymethyl, ethoxyl methyl, just-the propoxy-methyl, just-butoxymethyl; The methyl carbonyl, methyl sulphonyl; Optional separately by the identical or different fluorine that is selected from, chlorine, the substituting group one of methyl or trifluoromethyl or dibasic phenylcarbonyl group or benzyl; Perhaps represent cyclopropyl.X especially preferably represents oxygen or sulphur.One of group below Y especially preferably represents
-CH 2-,-CH(CH 3)-,-CH(C 2H 5)-,-CH(n-C 3H 7)-,CH(i-C 3H 7)-,-CH 2-CH 2-,
-CH(OH)-,-CH(OCH 3)-,-CH(O-CO-CH 3)-,-CH(CN)-,-CHF-,-CHCl-,
Figure A9719843000231
-CH-CH-or-CH 2O-.A particularly preferably
(1) representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is: halogen, nitro, cyano group, C 1-C 12-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 12-haloalkyl, C 1-C 4-alkoxyl group has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 2-C 4-alkenyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 2-C 4-halogenated alkenyl, following group
Figure A9719843000232
And phenoxy group, thiophenyl, benzyl oxygen base or pyridyl oxygen base, these groups are optional separately to be selected from one to three replacement of following substituting group by identical or different: halogen, nitro, cyano group, thiocarbamoyl, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkoxy-C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 1-C 4-alkylthio-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphonyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl, C 1-C 4-alkyl sulphonyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkyl sulfonyl, formyl radical, C 1-C 4-alkyl-carbonyl, C 1-C 4-alkoxy carbonyl, C 1-C 4-alkoxyl group imido grpup-C 1-C 2-alkyl, optional by C 1-C 2-alkyl replaces one of basic and following group of De oxadiazole-3-
Figure A9719843000241
(2) the optional cyclopentyl that is replaced by identical or different substituting group one to five of representative, cyclohexyl, cyclopentenyl or cyclohexenyl, possible substituting group is a fluorine, chlorine, bromine, methyl, ethyl, sec.-propyl, methoxyl group or trifluoromethyl,
(3) representative is optional by identical or different substituting group one or dibasic following heterocycle:
Figure A9719843000242
Suitable substituents is under the various situations: fluorine, chlorine, nitro, cyano group; Methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or tert-butyl; Methoxyl group, oxyethyl group, just-or different-propoxy-; Methylthio group;-CF 3,
-CHF 2,-CH 2CF 3,-CH 2-CF 2-CHF 2,-CH(CF 3)-CH 3；-OCF 3,
-OCHF 2,OCH 2CF 3,-O-CH 2-CF 2-CF 3,-OCH 2-CF 2-CHF 2,
-O-CH (CF 3)-CH 3-SCF 3And phenyl, phenoxy group or thiophenyl, these groups are optional separately to be replaced by identical or different substituting group one or two, and possible substituting group is: fluorine, chlorine, nitro, cyano group, methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; R wherein 8Represent C 1-C 4-alkyl, particularly methyl or ethyl; C 1-C 4-alkyl-carbonyl, particularly methyl carbonyl or ethyl carbonyl; And representative is optional by the identical or different C that is selected from 1-C 4-alkyl, particularly methyl or ethyl; Halogen, particularly fluorine or chlorine; C 1-C 4-haloalkyl, particularly trifluoromethyl; C 1-C 4-alkoxyl group, particularly methoxyl group; And C 1-C 4The substituting group one of-halogenated alkoxy, particularly trifluoromethoxy or dibasic phenyl sulfonyl; Perhaps
(4) representative connects as required, and optional by identical or different substituting group one below quaternary two-or three cyclic groups: Adamantyl
Figure A9719843000253
Substituting group possible under the various situations is: fluorine, chlorine, bromine, nitro, cyano group; Methyl, ethyl; Methoxyl group, methylthio group, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; R wherein 1Represent hydrogen, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, representative is optional by the identical or different fluorine that is selected from, chlorine, the C that the substituting group one to five of bromine and methyl replaces 3-C 7-cycloalkyl, perhaps representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a fluorine, chlorine, bromine, methyl, ethyl, just-or different-propyl group, methoxy or ethoxy, R 2And R 3Be identical or different, represent hydrogen separately, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl; R 4Represent methylidene, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, representative is optional by the identical or different fluorine that is selected from, chlorine, the substituting group one to five of bromine and methyl replaces the C of (preferred to three replaces) 3-C 7-cycloalkyl, perhaps representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a fluorine, chlorine, bromine, methyl, ethyl, just-or different-propyl group, methoxy or ethoxy; Represent oxygen or group=N-OR with W 5With=N-NR 6R 7One of, R wherein 5Represent C 1-C 4-alkyl or representative optional by identical or different substituting group one to trisubstituted benzyl, possible substituting group is a fluorine, chlorine, bromine, nitro, cyano group, trifluoromethyl, trifluoromethoxy, methylthio group, methylsulfinyl, methyl sulphonyl, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxy or ethoxy; And R 6And R 7Be identical or different, represent hydrogen, C separately 1-C 4-alkyl or representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a fluorine, chlorine, bromine, nitro, cyano group, methyl, ethyl, trifluoromethyl, methoxyl group or trifluoromethoxy.Q very particularly preferably represents one of following group Z wherein 1And Z 2Be identical or different, represent hydrogen separately, chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy.R very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxyl methyl, methyl carbonyl, phenylcarbonyl group or methyl sulphonyl.X very particularly preferably represents oxygen or sulphur.Y very particularly preferably represents-CH 2-.A very particularly preferably represent optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is: fluorine, chlorine, bromine, nitro, cyano group, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or different-propoxy-, just-, different-, secondary-or tert.-butoxy; Methylthio group, CF 3, OCF 3, OCHF 2, SCF 3, SCCl 2F; CH 2Br, CH 2Cl; Group
Figure A9719843000271
Also have phenoxy group, it is optional to be selected from one to three replacement of following substituting group by identical or different: fluorine, chlorine, bromine, nitro, cyano group, thiocarbamoyl, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or different-propoxy-, just-, different-, secondary-or tert.-butoxy; Methylthio group, methylthiomethyl, CF 3, OCF 3, OCHF 2, SCF 3, SCCl 2F; CH 2Br, CH 2C1, methoxycarbonyl, methylsulfinyl, methyl sulphonyl, trifluoromethyl sulfonyl or group
Figure A9719843000272
R wherein 1Represent hydrogen, methyl or ethyl; R 2And R 3Be identical or different, represent hydrogen or methyl separately; R 4Represent methylidene or ethyl; Represent oxygen or group=N-OR with W 5, R wherein 5Represent methylidene, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, perhaps represent on ring, optional by identical or different substituting group one to trisubstituted benzyl, possible substituting group is a fluorine, chlorine, bromine, nitro, cyano group, methyl, ethyl, methoxy or ethoxy.
The preferred compound of the present invention is formula (I A) to (I D) compound:
Figure A9719843000281
R wherein, Z 1And Z 2Have above-mentioned definition generally, preferably, especially preferably and very particularly preferably separately, and X 1, X 2, X 3, X 4And X 5Represent above-mentioned under A to phenyl and/or phenoxy group those groups as generally, preferably, especially preferably and very particularly preferably substituting group definition, and X 1, X 2, X 3And X 4Also can represent hydrogen.
Further preferred one group of compound is that wherein phenoxy group is positioned at NR-CO-CH 2-or NR-CS-CH 2Those compounds of the formula of-group contraposition (I A) to (I D) in these compounds, particularly preferably are those wherein substituent X 1, X 2, X 3And X 4Represent the compound of hydrogen.
Above-mentioned general or preferred group definition or explanation are applicable to end product and correspondingly are applicable to initiator and intermediate.These group definition can make up as required mutually, promptly also comprise the combination between each preferable range.
The present invention preferably wherein comprises the formula I compound as the combination of preferred (preferably) definition above-mentioned.
The present invention particularly preferably is the formula I compound that wherein comprises as the combination of particularly preferred definition above-mentioned.
The present invention very particularly preferably be the formula I compound that wherein comprises as the combination of very particularly preferably definition above-mentioned.
Above and in the group definition that hereinafter provides, alkyl, the situation of alkyl or alkenyl-also comprise and heteroatoms combination for example, for example, and alkoxyl group or alkylthio--whenever possible, can be straight or branched in all cases.
What list is the example of N-isothiazolyl-(sulphur) acid amides of new replacement to table 1 to 9: The compound of table 1 is corresponding to logical formula I compound, wherein
Figure A9719843000292
R=HX=OY=CH 2A=is following listed: Table 2 table 2 comprises logical formula I compound, wherein Y=CH (CH 3) Q, R, X and A=such as table 1 are listed.Table 3 table 3 comprises logical formula I compound, wherein
Figure A9719843000311
R, X, Y and A=such as table 1 are listed.Table 4 table 4 comprises logical formula I compound, X=SQ wherein, and R, Y and A=such as table 3 are listed.Table 5 table 5 comprises logical formula I compound, wherein
Figure A9719843000312
R, X, Y and A=such as table 1 are listed.Table 6 table 6 comprises logical formula I compound, wherein R, X, Y and A=such as table 1 are listed.Table 7 table 7 comprises logical formula I compound, wherein R, X, Y and A=such as table 1 are listed.Table 8 table 8 comprises logical formula I compound, wherein R=HX=OY=CH 2A=
Figure A9719843000322
Q=following listed:
Figure A9719843000323
Table 9 table 9 comprises logical formula I compound, wherein
Q, R, X and Y=such as table 8 are listed.
According to the formula of method (a) (I is a) in the compound, for example uses thieno-[2,3c] isothiazole-3-base-amine and [4-(4-cyano-benzene oxygen)]-phenyl-Acetyl Chloride 98Min. is an initiator, and then reaction process can be represented by following reaction formula:
In formula (I b) compound according to method (b), use for example thieno-[2,3c] isothiazole-3-base-[4-(4-nitrophenoxy)]-phenyl-ethanamide is initiator, and Lawesson ' s reagent (2,4-pair-(4-p-methoxy-phenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulphide) be vulcanizing agent, then reaction process can be represented by following reaction formula:
In formula (I b) compound of method according to (c), for example use thieno-[2,3c] isothiazole-3-base-amine and [4-(4-chloro phenoxy group)]-phenyl-methyl dithioacetate is an initiator, then reaction process can be represented by following reaction formula:
Figure A9719843000341
As the inventive method (a) and the formula II aminoisothiazoles that needs of the initiator (c) be known (referring to, GB1568377 for example; J.Chem.Res.Synop.1989,29; DE-A2713573; Can.J.Chem.1973 (51), 1742 or JP05070469) and/or can prepare (referring to, for example, above-mentioned reference) by currently known methods.
They also can be prepared as follows: for example, at alkali for example in the presence of pyridine or the triethylamine, make formula (V) amino-nitrile derivative earlier with the hydrogen sulfide reaction,
Figure A9719843000342
Wherein Het as above defines, and then with oxygenant H for example 2O 2, the formula VI thioamide derivatives that obtains of bromine or hypochlorite oxidation Wherein Het as above defines.
The amino-nitrile derivative of formula (V) be known (referring to, for example, EP-A0453611; ActaChim.Scand., Ser.B.1975, B29 (2), 224; DE-A2713573; Pharmaceutical chemistry communique (Chem.Pharm.Bull.) 1971,19,119; The tetrahedron communication, 1989,30,2631; J.Chem.Soc., Perkins Trans I, 1987,1521; Helv.Chim.Acta1975,58,2192; Pharmaceutical chemistry magazine (J.Med.Chem.) 1987,30,91; Heterocyclic chemistry magazine (J.Het.Chem.) 1985,22,1093 or EP-A0636626), and/or it can be by the preparation of known method (referring to, for example, above-mentioned reference).
Also the formula III acyl halide as the initiator in the inventive method (a) generally is known organic compound.In formula III, Hal preferably represents chlorine or bromine.
Also as the formula IV dithioesters of the initiator in the inventive method (c) be known (referring to, for example, tetrahedron 2663 (1984) or chemical research magazine (J.Chem.Research) (M) 2701 (1988)), and/or its can be by similar currently known methods preparation.In formula IV, the preferred represent methylidene of Alk.
Carry out the inventive method (a) preferable absorbent and be optional by halogenated aliphatic hydrocarbon or arene, ethers or nitrile, hexanaphthene for example, toluene, chlorobenzene, chloroform, methylene dichloride, ethylene dichloride ， diox, tetrahydrofuran (THF), ether or acetonitrile.
The suitable alkali that carries out method (a) is all conventional proton acceptors.Preferred basic metal or alkaline earth metal hydroxides, basic metal or alkaline earth metal carbonate or supercarbonate or the nitrogen base of using.The example that can mention is a sodium hydroxide, calcium hydroxide, salt of wormwood, sodium bicarbonate, triethylamine, dibenzyl amine, diisopropylamine, pyridine, quinoline, diazabicyclo octane (DABCO), diazabicyclo-nonene (DBN) and diazabicyclo hendecene (DBU).
Temperature of reaction in the inventive method (a) can change in the scope of broad.Generally speaking ,-40 ℃ and+carry out this reaction under the temperature between 200 ℃, preferably between 0 ℃ and 100 ℃.
When carrying out method (a), generally use the 1-2 mole, the formula III acyl halide of preferred 1-1.5 mole for the aminoisothiazoles of every mole of formula II.
In some cases, with the form of its halogen acid salt, for example, particularly hydrogen chlorate's form use formula II aminoisothiazoles is favourable.
Carrying out the preferred vulcanizing agent of the inventive method (b) is: and thiophosphoric anhydride or Lawesson ' s reagent [2,4-pair-(4-methoxyl group-phenyl)-1,3,2,4-dithia diphosphetan-2, the 4-dithione] (referring to, tetrahedron, Vol.41, No.22,5061 ff (1985)).
The preferred diluent of carrying out the inventive method (b) is a hydro carbons, for example toluene, dimethylbenzene, 1,2,3,4-tetralin, hexane or hexanaphthene.
When carrying out the inventive method (b), temperature of reaction can change in the scope of broad.Generally speaking, 0 ℃ and+carry out this reaction under the temperature between 200 ℃, preferably between 20 ℃ and 150 ℃.
When carrying out method (b), (I a) compound is generally used the 1-3 mole, preferred 1-2 mole vulcanizing agent for every mole of formula.Carry out aftertreatment by ordinary method.
The suitable diluent of carrying out the inventive method (c) is all conventional solvents.The preferred use chosen wantonly by halogenated fat hydrocarbon or arene, for example methylene dichloride, ethylene dichloride, hexanaphthene, toluene or chlorobenzene.
But, also can react without any solvent purely.
When carrying out the inventive method (c), temperature of reaction can change in the scope of broad.Generally speaking, 0 ℃ and+carry out this reaction under the temperature between 150 ℃, preferably between 20 ℃ and 120 ℃.
When carrying out the inventive method (c), generally use the 1-3 mole, preferred 1-1.5 mole formula IV dithioesters for every mole of formula II aminoisothiazoles.Carry out aftertreatment and separate by ordinary method.
Have good farm crop tolerance and the low active compound toxic of the present invention of warm-blooded animal is suitable for preventing and treating animal pest, agricultural particularly, forestry, the insect that stock protection and material protection and health field are run into, Arachnida and nematode.They preferably are used as the crop protection agent.These compounds all are activated for general susceptibility and resistance species, and effective in all stages or part stage that insect grows.Above-mentioned insect comprises: Isopoda (Isopoda), Oniscus aselluse for example, pillworm (Armadillidiumvulgare) and Porcellio scaber.Polypody detailed outline (Diplopoda), for example Blaniulus gutttulatus.Chcilopoda order (Chilopoda), for example Geophilus carpophagus and cricket Yan order kind (Scutigera spec.).Comprehensive detailed outline (Symphyla), for example Scutigerella immaculata.Thysanura (Thysanura), for example silverfiss (Lepisma saccharina).Collembola (Collembola), for example Onychiurus armatus.Orthoptera (Orthoptera), the non-Lian in east (Blatta orientalis) for example, periplaneta americana (Periplaneta americana), the non-Lian in Madeira (Leucophaea maderae), Groton bug (Blattella germanica), house cricket found in a kitchen (Acheta domesticus), Gryllotalpa spp (Gryllotalpa spp.), torrid zone migratory locusts (Locusta migratoriamigratorioides), long volume is born locust (Melanoplus differentialis) and Schistocerca gregaria.Dermaptera (Dermaptera), for example European earwig (Forficula auricularia).Isoptera (Isoptera), for example Cryptotermes (Reticulitermes spp.).Anoplura (Anoplura), head louse (Pediculus humanus corporis) for example, blind lice belongs to (Haematopinus spp.) and long volume lice (Linognathus spp.).Mallophaga (Mallophaga), for example Trichodectes (Trichodectes spp.) and Damalinea spp..Thysanoptera (Thysanoptera), for example greenhouse Hercinothrips spp (Hercinothripsfemoralis) and cotton thrips (Thrips tabaci).Heteroptera (Heteroptera), for example brown scutteleerid belongs to (Eurygasterspp.), Dysdercus intermedius, and beet is intended lace bug (Piesma quadrata), bedbug (Cimex lectularius), Rhodnius prolixus and triatoma sanguisuga belong to (Triatoma spp.).Homoptera (Homoptera), Aleurodes brassicae for example, whitefly in bt cotton (Bemisiatabaci), Trialeurodes vaporariorum Westwood (Trialeurodes vaporariorum), cotten aphid (Aphisgossypii), brevicoryne brassicae (Brevicoryne brassicae), the tea deer conceals knurl volume aphid (Cryptomyzus ribis), black bean aphid (Aphis fabae), apple aphid (Aphispomi), eriosoma lanigerum (Eriosoma lanigerum), mealy plum aphid (Hyalopterusarundinis), Phylloxera vastatrix, Pemphigus spp., Macrosiphumavenae, knurl volume aphid (Myzus spp.), hops knurl volume aphid (Phorodon humuli), grain Rhopalosiphum spp (Rhopasiphum padi), leafhopper belongs to (Empoasca spp.), Euscelisbilobatus, rice green leafhopper (Nephotettix cincticeps), brown apricot scale (Lecanium corni), Fructus oleae europaeae helmet (Saissetia oleae), rice small brown rice planthopper (Laodelphax striatellus), brown back rice plant hopper (Nilaparvata lugens), California red scale (Aonidiella aurantii), Aspidiotus hederae, mealybug belongs to (Pseudococcus spp.) and Psylla spp (Psylla spp.).Lepidopteran (Lepidoptera), for example, pink bollworm (Pectinophora gossypiella), loose looper (Bupalus piniarius), Cheimatobia brumata, Lithocolletis blancardella, cherry ermine moth (Hyponomeuta padella), small cabbage moth (Plutella maculipennis), tent caterpillar (Malacosomaneustria), Euproctis chrysorrhoea, Euproctis (Lymantria spp.), cotton shot hole of leaf lyonetid (Bucculatrix thurberiella), Phyllocnisticitrella, cutworm (Agrotis spp.), cutworm (Euxoa spp.), brown noctuid (Feltia spp.), earias insulana (Earias insulana), Noctua (Heliothisspp.), beet armyworm (Spodoptera exigua), lopper worm (Mamestrabrassicae), Panolis flammea, prodenia litura (Spodoptera litura), Noctua (Spodoptera spp.), cabbage looper (Trichoplusia ni), carpocapsa pononella (Carpocapsa pomonella), Pier (Pieris spp.), snout moth's larva (Chilospp.), Pyrausta nubilalis, Ephestia kuehniella, rheum officinale snout moth's larva (Galleria mellonella), bag casemaking clothes moth (Tineola bisselliella), etting moth (Tinea pellionella), brown oecophorid (Hofmannophilapseudospretella), Cacoecia podana, Capua reticulana, choristoneura fumigerana (Choristoneura fumiferana), grape codling moth (Clysia ambiguella) (Clysiaambiguella), tea yellow leaf curl moth (Homona magnanima) and the green leaf roller of oak (Tortrix viridana).Coleoptera (Coleoptera), for example, furniture death watch beetle (Anobium punctatum), Rhizopertha dominica, Bruchidius obtectus, bean weevil (Acanthoscelides obtectus), house longhorn beetle (Hylotrupes bajulus), Agelastica alni, first bell potato beetle (Leptinotarsa decemlineata), Phaedon cochleariae, chrysomelid genus (Diabrotica spp.), the blue flea beetle (Psylliodes chrysocephala) of rape, mexican bean ladybird (Epilachnavarivestis), Atomaria spp., saw chest ostomatid (Oryzaephilussurinamens), weevil belongs to (Anthonomus spp.), Sitophilus (Sitophilusspp.), Otiorrhynchus sulcatus, banana spider base weevil (Cosmopolitessordidus), Ceuthorrhynchus assimilis, lucerne place leaf weevil (Hyperaposttica), khapra beetle belongs to (Dermestes spp.), khapra beetle belongs to (Trogoderma spp.), khapra beetle belongs to (Anthrenus spp.), attagenus piceus (Attagenue spp.), powder moth (Lyctusspp.), Meligethes aeneus, Ptinus (Ptinus spp.), golden yellow ptinid (Niptus hdoleucus), wheat ptinid (Gibbium psylliodes) is intended paddy Oryza (Tribolium spp.), bloom first (Tenebrio molitor), click beetle belongs to (Agriotesspp.), acupuncture needle Eimeria (Conoderus spp.), Melolontha meiolontha, chafer in June (Amphimallon solstitialis) and Costelytra zealandica.The film wing belongs to (Hymenoptera), and for example Neodiprion spp belongs to (Diprion spp.), tenthredinidae (Hoplocampa app.), ant (Lasius spp.), kitchen ant (Monomoriumpharaonis), and wasp (Vespa spp.).Dipteron belongs to (Diptera), for example, squeak mosquito (Aedes spp.), spot Anopheles (Anophelesspp.), culex (Culex spp.), drosophila yellow gorilla (Drosophila melanogaster), housefly (Musca spp.), stable fly (Fannia spp.), calliphora erythrocephala (Calliphoraerythrocephala), lucilia sericata (Lucilia spp.), Chrysomyia spp., cuterbrid belongs to (Cuterebra spp.), Gastrophilus spp., Hyppobosca spp., Genus Stomoxys (Stomoxys spp.), the nose fly belongs to (Oestrus spp.), Hypoderma (Hydodermaspp.), the gadfly belongs to (Tabanus spp.), Tannia spp., Bibio hortulanus, Sweden's wheat stem chloropid fly (Oscinella frit), wheat fly (Phorbia spp.), beet fly (Pegomyia hyoscyami), Mediterranean fruitfly (Ceratitis capitata), dacus oleae (Dacus oleae) and European daddy-longlegs (Tipulapaludosa).Siphonaptera (Siphonaptera), for example, Xenopsyllacheopis (Xenopsylla cheopis), and Ceratophyllus (Ceratophyllus spp.).Arachnida (Arachnida), Sciopio maurus for example, black widow (Latrodectus mactans).Acarina (Acarina), for example, Acarus siro (Acarus siro), latent beak ant (Argasspp.), the beak tick belongs to (Ornithodoros spp.), Dermanyssus gallinae (Dermanyssusgallinae), Eriophyes ribis, citrus rust mite (Phyllocoptruta oleivora), Boophilus (Boophilus spp.), carrapato belongs to (Rhipicephalus spp.), Amblyomma (Amblyomma spp.), Hyalomma spp., hard ant (Ixodes spp.), the rice weevil mite belongs to (Psoroptes spp.), Trombidium (Chorioptes spp.), itch mite (Sarcoptes spp.), the line mite belongs to (Tarsonemus spp.), lucerne place tongue mite (Bryobia praetiosa), red spider (Panonychus spp.) and tetranychus telarius belong to (Tetranychus spp.).
Nematode comprises phytoparasite, for example Pratylenchidae belongs to (Pratylenchus spp.), similar similes thorne (Radopholus similis), fuller's teasel Ditylenchus dipsaci (Ditylenchusdipsaci), the nematode (Tylenchulus semipenetrans) of partly puncturing, Heterodera (Heterodera spp.), ball Heterodera (Globoders spp.), Meloidogyne (Meloidogyne spp.), Aphelenchoides (Aphelenchoides spp.), minute hand Turbatrix (Longidorus spp.), Xiphinema (Xiphinema spp.), burr Turbatrix (Trichodorus spp.).
Formula I compound of the present invention has the outstanding insect active that kills especially.
They are used to the insect of special successfully control injury plant, has strong activity, for example kill horseradish ape chrysomelid (Phaedon cochleariae) larva, meadow mythimna separata (Spodopterafrugiperda) caterpillar and kill rice green leafhopper (Nephotettix cincticeps).
Active compound can be transformed into conventional formulation, for example solution, emulsion, wettable powder, suspension, pulvis, pulvis subtilis, paste, soluble powder, granule, suspendible missible oil, be soaked with the natural and synthetic material of active compound and be wrapped in trickle capsule in the polymkeric substance.
These type agent can be produced in a known manner, are that liquid solvent and/or solid carrier mix with active compound with expanding agent for example and preferably, and optional tensio-active agent, i.e. emulsifying agent and/or dispersion agent and/or the pore forming material of using.
If use water as the expansion agent, also can use-case such as organic solvent make solubility promoter.Suitable liquid solvent mainly contains: aromatic substance, and as dimethylbenzene, toluene or alkylnaphthalene, chloro aromatic substance and chlorinated aliphatic hydrocarbon are as chlorinated benzene class, vinylchlorid or methylene dichloride, aliphatic hydrocarbon, as hexanaphthene or paraffin, mineral oil fraction for example, mineral oil and vegetables oil, alcohols, as butanols or ethylene glycol with and ether and ester, ketone, as acetone, methylethylketone, methyl iso-butyl ketone (MIBK) or pimelinketone, intensive polar solvent, as dimethyl formamide and methyl-sulphoxide, and water.
Suitable solid carrier is:
Ammonium salt for example, ground natural mineral matter such as kaolin, clay, talcum, chalk, quartz, attapulgite, montmorillonite or diatomite and ground synthetic mineral matter are as high dispersive silicon-dioxide, alumina and silicate; The solid carrier that is fit to that is used for granule has: for example crushing and broken natural mineral matter such as calcite, marble, float stone, sepiolite and rhombspar, and the synthetic particle of organic and inorganic powder and following organic particle: for example wood sawdust, coconut husk, corn cob and tobacco stem; The emulsifying agent and/or the pore forming material that are fit to have: for example nonionic and anionic emulsifier, as polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, for example, alkylaryl polyglycol ether, alkylsulfonate, alkyl-sulphate, arylsulphonate and protein hydrolysate; The dispersion agent that is fit to has: for example, and lignin sulfite waste liquor and methylcellulose gum.
In the preparation, can use the natural and synthetic polymer of tackiness agent such as carboxymethyl cellulose and powdery, particle or latex form, as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipid, as kephalin and Yelkin TTS, and synthetic phospholipid.Other possible additive can be mineral oil and vegetables oil.
Also can use dyestuff, as mineral dye, for example ferric oxide, titanium oxide and Prussian blue, and organic dye are as the salt of alizarine dyestuff, azoic dyestuff and metal phthalocyanine dyestuff and micro-nutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Generally speaking, preparation contains the active compound of 0.1-95% weight, preferred 0.5-90%.
Active compound of the present invention can be sold preparation and existed as the mixture with other active compound by the type of service of these formulation preparation with its merchant, for example sterilant, attractive substance, apholate, sterilant, miticide, nematocides, mycocide, growth regulator or weedicide.Sterilant comprises for example phosphoric acid ester, carbamate, carboxylicesters, hydrochloric ether, phenylurea and the compound that is prepared by microorganism.
Useful especially hybrid combination person for example be following listed those:
Mycocide:
The 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6 '-two bromo-2-methyl-4 '-trifluoromethoxy-4 '-Trifluoromethyl-1s, 3-thiazole-5-formylaniline; 2,6-two chloro-N-(4-trifluoromethyl benzyl) benzamide; (E)-2-methoxyl group imido grpup-N-methyl-2-(2-Phenoxyphenyl)-ethanamide; Oxine vitriol; (E)-2-{2-[6-(2-cyano-benzene oxygen)-pyrimidine-4-base oxygen base]-phenyl }-the 3-methoxy-methyl acrylate; (E)-methoxyl group imido grpup [α-(o-tolyl oxygen base)-o-tolyl] methyl acetate; 2-phenylphenol (OPP), aldimorph, ammonia third phosphoric acid, anilazine, penta ring azoles,
M 9834, adjacent iodoxy aniline, F-1991, Niagara 9044, biphenyl, Bitertanol, miewensu, bromuconazole, bupirimate, the fourth Saite,
Lime sulfur mixture, Difolatan, Vancide 89, derosal, carboxin, chinomethionate, chloroneb, trichloronitromethane, hundred bacterium disappear, chlozolinate, maneb, frost urine cyanogen, cyproconazole, cyprofuram,
Dichlorophen, diclobutrazol, diclofluanid, diclomezine, dicloran, the mould prestige of second, Difenoconazole, the phonetic fen of diformazan, the olefin(e) acid morpholine, alkene azoles alcohol, dinitrocrotonate, pentanoic, pyrrole bacterium sulphur, ditalimfos, the Delan, dodine ， An azolactone,
Hinosan, epoxyconazole, the phonetic phenol of second, etridiazole,
Fenarimol, fenbuconazole, first furan anilide is planted the clothing ester, fenpiclonil, fenpropidin, fenpropimorph, triphenyl tin acetate, fentin hydroxide, Karbam Black, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, fluzilazol, flusulfamide, fultolanil, flutriafol, Phaltan, phosethyl Al, phthalide, fuberidazole, furalaxyl, seed dressing amine, seed-grain is fixed
Perchlorobenzene, own azoles Chun ， hymexazo,
Press down mould azoles, the acid amides azoles, bivalve acetate, iprobenfos (IBP), RP-26019, isoprothiolane,
Kasugamycin, copper agent, for example: copper hydroxide, copper naphthenate, COPPER OXYCHLORIDE 37,5, copper sulfate, cupric oxide, copper 8-quinolinolate and Bordeaux mixture,
Mancopper, maneb, zinc manganese ethylenebisdithiocarbamate, mepanipyrim, mebenil, metaxanin, metconazole, methasulfocarb, methuroxam, Carbatene, metsulfovax, nitrile bacterium azoles,
Dimethyl dithiocarbamate nickel, nitrotha]-isopropyl, nuarimol,
The spirit of fenfuram ， Evil frost, oxamocarb, oxycarboxin,
Pefurazoate, Topaze, pencycuron, rice blast phosphorus, phthalide, myprozine, disease is spent spirit, polyurethane(s), Polyoxin, the sick isothiazole of alkene, delicious peace, procymidone, propionic acid amide encircles third azoles, zinc 1,2-propylene bisdithiocarbamate, the phonetic phosphorus of pyrrole, pyrifenox, pyrimethanil, pyroquilon,
Quintozene (PCNB),
Sulphur and sulphur preparation,
Tebuconazole, tecloftalam, tecnazene, the phonetic azoles of fluorine, thiabendazole, thicyofen, thiophanate_methyl, thiram, tolclofosmethyl, methyl fluoride sulfanilamide (SN), triazolone, triadimenol, azoles bacterium piperazine, poplar bacterium amine, tricyclazole, tridemorph, fluorine bacterium azoles, triforine, triticonazole,
Validamycin, Vinclozoline,
Zineb, ziram.
Bactericide:
Bronopol, dichlorophen, chloromethylpyridine, dimethyl dithiocarbamate nickel, kasugamycin, isothiazolones, furancarboxylic acid, oxytetracycline, different third thiazole of alkene, Streptomycin sulphate, tecloftalam, copper sulfate and other copper agent.
Insecticide/miticide/nematocides:
Avermectin, AC303630, acephate, fluorine ester chrysanthemum ester, alanycarb, aldicarb, the nail body Cypermethrin, two worm amidines, avermectins, AZ60541, azadirachtin, azinphos-A, azinphos-methyl, azocyclotin,
Bacillus thuringiensis ， Evil worm prestige, benfuracarb, bensultap, cyfloxylate, bifenthrin, BPMC, brofenprox, bromofos, bufencarb, Buprofezin, butocarboxim, butylpyridaben,
Cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, CGA157419, CGA184699, chloethocarb, chlorethoxyfos, Zaprawa enolofos, UC 62644, chlormephos, Chlorpyrifos 94, chlorpyrifos_methyl, cis-resmethrin, clocythrin, four mite piperazines, cynock, cycloprothrin, cyfloxylate-β, cyhalothrin, cyhexatin, Cypermethrin, fly eradication amine
Deltamethrin, Systox-M, Systox-S, demeton_S_methyl, methamidophos, diazinon, phenol line phosphorus, SD-1750, dicliphos, Carbicron, Nialate, diflubenzuron, Rogor, dimethylvinphos, Kavadel, thiodemeton,
Hinosan, emamectin, esfenvalerate, ethiofencarb, Nialate, ether chrysanthemum ester, ethoprophos, etrimfos,
Worm amine phosphorus, fenazaquin, fenbutatin oxide, fenitrothion 95, fenobucarb, fenothiocarb, ABG-6215, Cypermethrin, fenpyrad, azoles mite ester, Tiguvon, fenvalerate, fipronil, fluazifop, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, taufluvalinate, N-2790, peace fruit, lythidathion, fubfenprox, furathiocarb
HCH, heptenopos, fluorine bell urea, hexythiazox,
Provado, iprobenfos, isazofos, isofenphos, Ro 7-5050 ， oxazole phosphorus, ivermectin, cyhalothrin, lufenuron,
The Malathion, mecarbam, Phosdrin, mesulfenphos, Halizan, methacrifos, acephatemet, methidathion, methiocarb, methomyl, meta-tolyl-N-methylcarbamate (MTMC), milbemectin, monocrotophos, moxidectin,
Naled, NC184, NI25, nitenpyram,
Omethoate, oxamyl, oxydemeton-methyl, Thiometan,
Thiophos-A, thiophos-M, permethrin, Tsidial, phorate, Phosalone, R-1504, phosphamidon, Volaton, anti-bud prestige, pririmiphos_methyl, Pyrimithate-A, Profenofos, promecarb, Kayaphos, Propoxur, Toyodan, Fac, pymetrozin, pyraclofos, pyradaphenthion, pyresmethrin, pyrethrin, pyridaben, pyrimidifen, pyriproxyfen
Resitox,
RH5992，
Dioxabenzofos, sebufos, silafluofen controls snout moth's larva sulphur phosphorus, the first Toyodan,
Tebufenozid, tebufenpyrad, tebupirimiphos, fluometuron, tefluthrin, temephos, spy's prestige of going out, Terbufos, tetrachlorvinphos, thiafenox, the two prestige of sulphur, monocrotophos, thiometon, thionazin, thuringiensin, tralomethrin, benzene thiophene mite, triazophos, triazuron, Trichlorphon, desinsection is grand, dimethacarb
Bud goes out many, XMC, xylylcarb, YI5301/5302, zetamethrin.
Also can be and other known active compound weedicide for example, perhaps with the mixture of fertilizer and growth regulator.
Active compound of the present invention can also be sold preparation and exists as the mixture with synergistic agent with the type of service by these formulation preparation with its merchant.Synergistic agent is to improve the effect of active compound and itself need not to be active compound.
The active compound content of being sold the type of service of formulation preparation by the merchant can change in wide region.The concentration of type of service active compound is the 0.0000001-95% weight active compound, preferred 0.0001-1% weight.
Use these compounds with the usual manner that is suitable for these types of service.
When being used for killing health field insect and stored prod insect, these active compounds have the fabulous residual action to timber and clay, and to the good stability with the alkali on the material of lime treatment.
Active compound of the present invention is not only to plant, and health field and stored prod insect have activity, but also are used for field of veterinary, kills zooparasite (epizoa), for example hard tick, soft ticks, psoroptes equi, trombiculid, fly (sting and suck), tachinid larva, lice, head louse, bird lice and flea.Such parasite comprises:
Anoplura (Anolpurida), for example, Haematopinus (Haematopinus spp.), Linognathus spp (Linognathus spp.), lice belongs to (Pediculus spp.), Pthirus (Phtirusspp.), the pipe lice belongs to (Solenopotes spp.).
Mallophaga is stung lice (Mallophagida) and Amblycerina and Ischnocerina suborder, for example the hair Trichodectes (Trimenopon spp.), Menopon spp., huge Trichodectes (Trinoton spp.), Bovicola (Bovicola spp.), Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felcolaspp..
Diptera (Diptera) and Nemocera (Nematocerina) and Brachycerina suborder, yellow-fever mosquito (Aedes spp.) for example, spot Anopheles (Anopheles spp.), culex (Culex spp.), Simulium (Simulium spp.), the true buffalo gnat of all woolen (Eusimulium spp.), sand fly (Phlebotomus spp.), Lutzomyia (Lutzomyia spp.), storehouse midge (Culicoides spp.), spot horsefly (Chrysops spp.), knurl horsefly (Hybomitra spp), Atylotus spp., Gadfly (Tabanus spp.), Chrysozona (Haematopotaspp.), Philipomyia spp., Braula spp., Musca spp., Hydrotaea (Hydrotuea spp.), sting fly (Stomoxys spp.), Haematobia spp., Morellia spp., latrine fly (Fannia spp.), Glossina spp., Calliphoraspp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., other sarcophagid (Sarcophaga spp.), Oestrus spp., torsalo (Hypoderma spp.), Gasterophilus spp., hippoboscid (Hippobosca spp.), Lipoptena spp. and Melophagus spp..
Siphonaptera (Siphonapterida), for example, flea belongs to (Pulex spp.), Ctenocephalides spp., mouse flea (Xenopsylla spp.), and c. leaf flea (Ceratophyllus spp.).
Heteroptera (Heteropterida), for example, Cimex (Cimex spp.), triatoma sanguisuga belongs to (Triatoma spp.), Rhodnius spp., and Panstrongylus (Panstrongylusspp.).
Non-Lian order (Blattarida), the non-Lian in east (Blatta orientalis) for example, periplaneta americana (Periplaneta americana), Groton bug (Blattela germanica), non-Lian belongs to (Supella spp.).
Mite subclass (Acarida), with metaspiracle order (Metastigmata) and mesostigma order (Mesostigmata), for example, latent beak tick belongs to (Argas spp.), the beak tick belongs to (Ornithodorus spp.), ear tick (Otabius spp.), hard tick (Ixodesspp.), Amblyomma (Amblyomma spp.), Boophilus (Boophilus spp.), Dermacentor (Dermacentor spp.), Haemophysalis spp., glass eye tick (Hyalomma spp.), carrapato belongs to (Rhipicephalus spp.), Dermanyssus gallinae (Dermanyssus spp.), auspicious upright tapeworm (Raillietia spp.), Pneumonyssusspp., Sternostoma spp. and Varroa spp..
Actinedida (Trombidiformes, Prostigmata) and Acaridida (Astigmata), Acarapis spp. for example, Cheyletiella (Cheyletiella spp.), Ornithocheyletia spp., Myobia spp., itch mite (Psorergates spp.), demodicid mite (Demodex spp.), trombiculid (Trombicula spp.), Listrophorusspp., Acarus siro (Acarus spp.), junket mite (Tyrophagus spp.), have a liking for wooden mite (Caloglyphus spp.), Hypodectes spp., wing clothing mite belongs to (Pterolichusspp.), trombiculid (Psoroptes spp.), trombiculid (Chorioptes spp.), Octodectes spp., itch mite (Sarcoptes spp.), Notoedres spp., foot mite (Knemidocoptes spp.,), Cytodites spp., and Laminosioptesspp..
Formula I active compound of the present invention also is suitable for killing the arthropods of infecting the agriculture production domestic animal, and described domestic animal is an ox for example, sheep, goat, horse, pig, donkey, camel, buffalo, rabbit, chicken, turkey, duck, goose, honeybee, other pet, dog for example, cat, bird of raising in cages and fish jar are cultured fish and are referred to as the animal of laboratory animal, for example hamster, cavy, rat and mouse.By preventing and treating these arthropodss, can reduce the dead and raising output (for example meat is suckled, hair, skin, egg, honey etc.) of domestic animal, so the application of the invention active compound can be realized more economical simpler animal rearing.
In field of veterinary, active compound of the present invention uses by enteral administration in a known way, for example with tablet, capsule, draught, draught, granule, paste, bolus, by sending the food method, suppository passes through parenteral administration, for example pass through to inject (intramuscular, subcutaneous, intravenously, intraperitoneal etc.), imbed, pass through nasal administration, by with for example dipping or dipping bath, spray, the Shi Hedian that falls executes, wash with and the form percutaneous drug delivery of dusting, also can be by means of the moulded products that contains active compound neck ring for example, ear pendant, tailpiece, the bottom bands of trouser legs, halter, marker etc. and using.
When to livestock, poultry, when pets etc. are used, formula I active compound of the present invention can be used as the preparation (pulvis for example that contains active compound with the amount of 1-80% weight ratio, emulsion, but flowing agent) be used, directly use or doubly back use of dilution 100-10000, perhaps can use with the form of chemical bath.
In addition, find that also formula I compound of the present invention also has the strong insecticidal action of the insect of destroying Industrial materials extremely.
As an example, preferably can mention following insect, but not limited:
Beetle, for example
House longhorn beetle (Hylotrupes bajulus), Chlorophorus pilosis, furniture death watch beetle (Anobium punctatum), Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobiumcarpini, European bamboo powder moth (Lyctus brunneus), Lyctus africanus, flat neck powder moth (Lyctus planicollis), Lyctus linearis, Lyctuspubescens, Trogoxylon aequale, Minthes rugicollis, bark beetle kind (Xyleborus spec.), Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus branneus, Simoxylonspec., and dinoderus minutus (Dinoderus minutus).
Hymenoptera (Dermapterans), for example
The blue or green little wood wasp (Sirex juvencus) of steel, the big wood wasp of fir (Urocerus gigas), Urocerus gigas taignus and Urocerus augur.
Termite, for example
Kalotermes flavicollis, Cryptotermes brevis, Heterotermesindicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Australia termite (Mastotermesdarwiniensis), Zootermopsis nevadensis and coptotermes formosanus of taiwan (Coptotermes formosanus).
Bristle-tail, for example silverfiss (Lepisma saccharina).
Related Industrial materials are interpreted as non-living material among the present invention, for example, and preferred synthetic materials, tackiness agent, sizing material, paper and cardboard, leather, timber and wood working product and coating.
Its material that is not subjected to infestation by insect that makes that will protect very especially is timber and wood working product.
Can or contain a kind of like this timber of mixture protection of composition and the wood working product is interpreted as and is with the present composition, construction timber processed goods for example, wooden frame; sleeper, bridge construction timber, harbour; wooden launch vehicle, chest, pallet; container, electric pole, wooden barrel; timber window, timber, glued board; particle board, joiner is perhaps in the Wood products of building construction or the very common use of joinery.
Active compound of the present invention can be with itself, with missible oil form or general for example pulvis, granule, solution, suspension, emulsion or paste use of conventional formulation.
Described preparation can be with known method preparation itself, for example by mixed active compound and at least a solvent or thinner, emulsifying agent, dispersion agent and/or tackiness agent or fixing agent, water-resisting agent, if suitable, siccative and UV stablizer and, if suitable, tinting material and pigment and other processing aid.
Be used to protect the insecticides of timber and woodwork or concentrate to contain active compound of the present invention, particularly 0.001-60% weight with the 0.0001-95% weight concentration.
The composition that uses or the amount of concentrate depend on the species of insect with a situation arises, and depend on medium.Can decide by series of trials under every kind of situation of the optimum proportion of using.But, generally speaking, using 0.0001-20% weight based on the material that will protect, the active compound of preferred 0.001-10% weight is enough.
Solvent that uses and/or thinner be organic chemistry solvent or solvent mixture and/or oil or oil type low volatile organic learn solvent or solvent mixture and/or polar organic learn solvent or solvent mixture and/or water and, if suitable, emulsifying agent and/or wetting agent.
The preferred organic chemistry solvent that uses is to have greater than 35 volatilization number and be higher than 30 ℃, preferably is higher than the oil or the oil type solvent of 45 ℃ flash-point.As have low volatility and in water undissolved this class oil and oil type solvent and the material that uses is suitable mineral oil or its aromatic hydrocarbon fraction, perhaps contain the solvent mixture of mineral oil, preferably petroleum solvent, oil and/or alkylbenzene.
Advantageously the material of Shi Yonging is that boiling spread is 170-220 ℃ a mineral oil, and boiling spread is 170-220 ℃ a petroleum solvent, and boiling spread is 250-350 ℃ a spindle oil, and boiling spread is 160-280 ℃ oil or an aromatic substance, the terebene wet goods.
In preferred embodiments, the material of use is that boiling spread is 180-210 ℃ liquid aliphatic hydrocarbon or the boiling spread aromatic hydrocarbon that is 180-220 ℃ and high boiling mixture and/or the spindle oil and/or the naphthalene monochloride of aliphatic hydrocarbon, preferred α-naphthalene monochloride.
Have greater than 35 volatilization number and be higher than 30 ℃, the low volatility organic oil or the oil type solvent that preferably are higher than 45 ℃ of flash-points can partly replace to high volatile volatile or medium volatile organic chemistry solvent, prerequisite is that this solvent mixture also has greater than 35 volatilization number and is higher than 30 ℃, preferably be higher than 45 ℃ flash-point, and desinsection/fungicidal mixtures is soluble or emulsible in this solvent mixture.
In preferred embodiments, part organic chemistry solvent or solvent mixture replace to the aliphatics polar organic and learn solvent or solvent mixture.The preferred material that uses is the aliphatics organic chemistry solvent with hydroxyl and/or ester group and/or ether, glycol ether for example, ester etc.
The organic chemistry tackiness agent that uses in the scope of the invention is itself known synthetic resins and/or bonding dry oil, and can dilute with water and/or in the organic chemistry solvent that uses, be soluble, dispersible or emulsible, particularly following material is formed or contained to tackiness agent by following material: acrylic resin, ethenoid resin, polyvinyl acetate for example, vibrin, polycondensation or polyaddition resin, urethane resin, the Synolac of Synolac or modification, phenolic resin, hydrocarbon resin, for example indenes/coumarone resin, silicone resin, dried plant oil and/or dry oil and/or based on the physical dryness tackiness agent of natural and/or synthetic resins.
Can be as the synthetic resins that tackiness agent uses with emulsion, the form of dispersion liquid or solution is used.The pitch of maximum 10% weight or bituminous substances also can be used as tackiness agent and use.In addition, also can the known tinting material of use itself, pigment, water-resisting agent, smell are sheltered material and inhibitor or anticorrosive agent etc.
According to the present invention, composition or concentrate preferably contain the Synolac of at least a Synolac or modification and/or dried plant oil as the organic chemistry tackiness agent.According to the present invention, the preferred material that uses be oil-contg greater than 45% weight, the Synolac of preferred 50-68% weight.
The all or part of of tackiness agent above-mentioned can replace to fixing agent (mixture) or softening agent (mixture).These additives are for the volatilization that prevents active compound and crystallization or precipitation.The tackiness agent of the preferred 0.01-30% of replacement (based on 100% tackiness agent that uses).
Softening agent is from the phthalate of chemical grade, dibutyl phthalate for example, dioctyl phthalate (DOP) or benzyl phthalate butyl ester, phosphoric acid ester, tributyl phosphate for example, adipic acid ester, for example hexanodioic acid two-(2-ethylhexyl) ester, stearate, for example butyl stearate or amyl stearate, oleic acid ester, for example butyl oleate, the glycol ethers of glyceryl ether or higher molecular weight, glyceryl ester and p-toluenesulfonic esters.
The chemical fundamentals of fixing agent is the polyvinyl alkyl oxide, for example, and polyvinyl methyl ether, or ketone, for example benzophenone or ethylene benzophenone.
Also have water as solvent or thinner are specially suitable, if suitable, with one or more above-mentioned organic chemistry solvent or thinner, the mixture of emulsifying agent and dispersion agent uses.
Especially effectively the wood protection effect is to realize by a large amount of industrialization dipping methods, vacuum for example, two vacuum or pressure method.
If suitable, the instant composition can also contain other sterilant and, if suitable, another or multiple mycocide.
Sterilant and mycocide that can blended suitable supplementary component is preferably mentioned among the WO94/29268.The compound of mentioning in the document is introduced the application as a reference clearly.
Can blended composition very particularly preferably be sterilant, for example poison barnyard grass, Volaton with poison, silafluofin, nail body Cypermethrin, cyfloxylate, Cypermethrin, Deltamethrin, permethrin, Provado, NI-25, flufenoxuron, fluorine bell urea and desinsection are grand, and mycocide, for example epoxyconazole, own azoles alcohol, penta ring azoles encircles third azoles, tebuconazole, cyproconazole, metconazole, press down mould azoles, dichlofluanid, Tolylfluanid, carboxylamine 3-iodo-2-propynyl butyl ester, N-octyl group-isothiazoline-3-ketone and 4,5-two chloro-N-octyl group isothiazoline-3-ketone.
The preparation of active compound of the present invention and application can illustrate by the following examples.Preparation EXAMPLE Example 1 (method a)
In 15ml pyrimidine and 50ml acetonitrile, drip 3.50g (0.012mol) [4-(4-nitrophenoxy)]-phenyl chloride solution in the 20ml acetonitrile in 1.60g (0.01mol) thieno-[2,3c] isothiazole-3-base-amine aqueous solution.This mixture stirred 18 hours down at 25 ℃, then was concentrated into dried.Reaction mixture is dissolved in water/ethyl acetate, and with 10% aqueous sodium hydroxide solution repetitive scrubbing organic phase.After dry and concentrated, obtaining the heavy-gravity resistates, by the silica gel chromatography purifying, is moving phase with dichloromethane/ethyl acetate (20: 1).
Obtain 0.24g (theoretical amount 20%) thieno-[2,3c] isothiazole-3-base-[4-(4-nitrophenoxy)]-phenyl-acetamides, 223 ℃ of fusing points.
Similarly, and/or, obtain following formula I compound according to general preparation explanation:
Figure A9719843000502
*) m.p. (℃) or 1HNMR, δ ppm, d 6-DMSO) Application Example embodiment A daikon leaf beetle (Phaedon) larva test solvent: 7 parts of weight dimethyl formamide emulsifying agents: 1 part of weight alkylaryl polyglycol ether
In order to prepare the active compound appropriate formulation, with 1 part of weight active compound and described amount solvent and described amount emulsifier mix, water is diluted to missible oil the concentration that needs.
By handling cabbage leaves (Brassica oleracea) in the preparation of active compound that is immersed in expectation concentration, and standby horseradish ape chrysomelid (Phaedon cochleariae) larva is infected when leaf is also moistening.
Behind the certain hour, measure and kill percentage.The all mealworms of 100% expression all are killed; A mealworm is not killed in 0% expression.
In this test, under illustrative 0.1% activity compound concentration, the compound that for example prepares embodiment 2 reached 100% kill ratio after 7 days.Embodiment B meadow mythimna separata (Spodoptera Frugiperda) test solvent: 7 parts of weight dimethyl formamide emulsifying agents: 1 part of weight alkylaryl polyglycol ether
In order to prepare the active compound appropriate formulation, with 1 part of weight active compound and described amount solvent and described amount emulsifier mix, water is diluted to missible oil the concentration that needs.
By handling cabbage leaves (Brassica oleracea) in the preparation of active compound that is immersed in expectation concentration, and standby meadow mythimna separata (Spodoptera frugiperda) caterpillar is infected when leaf is also moistening.
Behind the certain hour, measure and kill percentage.The all caterpillars of 100% expression all are killed; A caterpillar is not killed in 0% expression.
In this test, under illustrative 0.1% activity compound concentration, the compound that for example prepares embodiment 2 reached 100% kill ratio after 7 days.Embodiment C leafhopper (Nephotettix) test solvent: 7 parts of weight dimethyl formamide emulsifying agents: 1 part of weight alkylaryl polyglycol ether
In order to prepare the active compound appropriate formulation, with 1 part of weight active compound and described amount solvent and described amount emulsifier mix, water is diluted to missible oil the concentration that needs.
By handling rice seedling (Oryzaesativa) in the preparation of active compound that is immersed in expectation concentration, and standby rice green leafhopper (Nephotettixcincticeps) larva is infected when seedling is also moistening.
Behind the certain hour, measure and kill percentage.The all leafhopper of 100% expression all are killed; A leafhopper is not killed in 0% expression.
In this test, under illustrative 0.1% activity compound concentration, the compound that for example prepares embodiment 2 reached 100% kill ratio after 6 days.

Claims (10)

1. formula I compound
Figure A9719843000021
Wherein Q represents group
Figure A9719843000022
Wherein substituted heterocycle is chosen in the Het representative wantonly; R represents hydrogen; alkyl; haloalkyl; alkoxyalkyl, alkyl-carbonyl, alkyl sulphonyl; the optional separately substituted aryl carbonyl of representative; aryl sulfonyl or arylalkyl, perhaps substituted cycloalkyl is chosen in representative wantonly, and X represents oxygen or sulphur; the optional substituted alkylidene group of Y representative; alkylene group, alkylidene group oxygen base or alkylidene group sulfenyl and the optional substituted aryl of A representative; optional substituted cycloalkyl, optional substituted cycloalkenyl group or optional substituted heterocycle.
2. the formula of claim 1 (I) compound, wherein Q represents group
Figure A9719843000023
Wherein Het representative has for example N of 1 or 2 hetero atom, S and O atom, optional by identical or different substituting group one to trisubstituted 5-or 6-unit heterocycle, possible substituting group is halogen, C1-C 4-alkyl, C1-C 4-alkoxyl, have for example fluorine of 1-5 identical or different halogen atom, the C of chlorine and bromine atoms1-C 4-haloalkyl, C1-C 4-alkoxy-C1-C 4-alkyl, nitro, C1-C 4-alkyl sulfonyl base, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 4-halogenated alkyl sulfonyl, also have thiocarbamoyl, and R represents hydrogen, C1-C 4-alkyl, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 4-haloalkyl, C1-C 4-alkoxy-C1-C 4-alkyl, C1-C 4-alkyl carbonyl, C1-C 4-alkyl sulfonyl base, represent phenylcarbonyl group, phenyl sulfonyl or benzyl, and it is chosen wantonly on benzyl ring separately by one to three replacement of identical or different substituting group, and possible substituting group is halogen in all cases, nitro, cyano group, C1-C 4-alkyl, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 2-haloalkyl, C1-C 4-alkoxyl, C1-C 4-alkylthio group, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 2-halogenated alkoxy, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 2-halogenated alkylthio, perhaps representative is optional by the identical or different C that is selected from1-C 4The substituting group one of-alkyl and halogen is to trisubstituted C3-C 6-cycloalkyl, X represents oxygen or sulphur, Y represents C1-C 6-alkylidene, C1-C 6-hydroxy alkylidene, C1-C 4-alkoxy-C1-C 6-alkylidene, C1-C 4-alkyl-carbonyl oxygen base-C1-C 6-alkylidene, cyano group-C1-C 6-alkylidene, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 4-halo alkylidene; Optional by the identical or different fluorine that is selected from, the substituting group one of chlorine and methyl is to trisubstituted C3-C 6-cycloalkyl-C1-C 4-alkylidene, C2-C 4-alkylene group, C1-C 4-alkylidene oxygen base or C1-C 4-alkylidene sulfenyl, A (1) representative optional by identical or different substituting group one to trisubstituted phenyl, possible substituting group is: halogen, nitro, cyano group, C1-C 12-alkyl, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 12-haloalkyl, C1-C 12-alkoxyl, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 12-halogenated alkoxy, C1-C 12-alkylthio group, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 12-halogenated alkylthio, C2-C 12-alkenyl, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 12-halogenated alkenyl, optional by the identical or different C that is selected from1-C 4The substituting group one of-alkyl and halogen is to trisubstituted C3-C 8-cycloalkyl, following groupAlso has phenyl, phenoxy group, thiophenyl, benzyl, benzyl oxygen base; pyridine radicals oxygen base, pyrimidine radicals oxygen base, pyrazinyl oxygen base or pyridazinyl oxygen base, these groups are optional separately is selected from one to three replacement of following group by identical or different: halogen; nitro, cyano group, thiocarbamoyl, C1-C 4-alkyl, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 4-haloalkyl, C1-C 4-alkoxyl, C1-C 4-alkoxy-C1-C 4-alkyl, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 4-halogenated alkoxy, C1-C 4-alkylthio group, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 4-halogenated alkylthio, C1-C 4-alkylthio group-C1-C 4-alkyl, C1-C 4-alkyl sulfinyl-C1-C 4-alkyl, C1-C 4-alkyl sulfonyl base-C1-C 4-alkyl, C1-C 4-alkyl sulfinyl, C1-C 4-alkyl sulfonyl base, have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-51-C 4-halogenated alkyl sulfonyl, formoxyl, C1-C 4-alkyl carbonyl, C1-C 4-alkoxyl carbonyl, C1- C 4-alkoxyl imido grpup-C1-C 4-alkyl, optional by C1-C 4One of-alkyl-replacement De oxadiazolyl or following group
(2) the optional C that is replaced by identical or different substituting group one to five of representative 5-C 8-cycloalkenyl group or C 3-C 8-cycloalkyl, possible substituting group is C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 3-C 8-cycloalkyl, and optional by the identical or different halogen that is selected from, nitro, cyano group, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group and have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4The substituting group one of-halogenated alkoxy is to trisubstd phenyl;
(3) representative has for example N of 1-3 heteroatoms, and S and O atom can randomly also contain one or more CO and/or CS group for becoming ring members, and it is optional by identical or different substituting group-to trisubstituted 5-or 6-unit heterocycle, possible substituting group is: halogen, nitro, cyano group, C 1-C 4-alkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, perhaps representative optional separately by identical or different substituting group one to trisubstd phenyl, phenoxy group, thiophenyl or benzyl, possible substituting group is: halogen, nitro, cyano group, C 1-C 4-alkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio; And wherein the N-H group that can randomly replace hydrogen atom to be present in the heterocycle can be by C 1-C 6-alkyl, C 1-C 6-alkyl-carbonyl or phenyl sulfonyl replace, and these substituting groups can be randomly by C 1-C 6-alkyl, halogen has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group or have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy replaces;
(4) representative contains for example N of one or more heteroatomss, S or O atom, and perhaps one or more CO groups are for becoming ring members, and the optional condensed two that is replaced by identical or different substituting group one to five-or three cyclic groups, possible substituting group is: halogen, nitro, cyano group, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxy-C 1-C 4-alkyl, C 1-C 4-alkoxyl group has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 1-C 4-alkyl sulphinyl, C 1-C 4-alkyl sulphonyl, hydroxyl, sulfydryl, C 1-C 4-alkyl-carbonyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkyl carbonyl, C 1-C 4-carbalkoxy or optional separately by one to three replacement of identical or different substituting group, particularly at the substituted phenyl of phenyl moiety, phenoxy group, thiophenyl or benzyl, possible substituting group is: halogen, nitro, cyano group, C 1-C 4-alkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio; R wherein 1Represent hydrogen, C 1-C 8-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, representative is optional by identical or different halogen and the C of being selected from 1-C 4The substituting group one of-alkyl or polysubstituted C 3-C 7-cycloalkyl, perhaps representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a halogen, C 1-C 4-alkyl or C 1-C 4-alkoxyl group, R 2And R 3Be identical or different, represent hydrogen or C separately 1-C 4-alkyl; R 4Represent C 1-C 8-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, representative is optional by identical or different halogen and the C of being selected from 1-C 4The substituting group one of-alkyl or polysubstituted C 3-C 7-cycloalkyl, perhaps representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a halogen, C 1-C 4-alkyl or C 1-C 4-alkoxyl group; Represent oxygen or group=N-OR with W 5With=N-NR 6R 7One of, R wherein 5Represent C 1-C 6-alkyl or representative are optional by the identical or different halogen that is selected from, nitro, cyano group, thiocarbamoyl, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkoxy-C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 1-C 4-alkylthio-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphonyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl, C 1-C 4-alkyl sulphonyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkyl sulfonyl, formyl radical, C 1-C 4-alkyl-carbonyl, C 1-C 4-alkoxy carbonyl and C 1-C 4-alkoxyl group imido grpup-C 1-C 4The substituting group one of-alkyl is to trisubstituted benzyl; And R 6And R 7Be identical or different, represent hydrogen, C separately 1-C 6-alkyl or representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a halogen, nitro, cyano group, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group or have for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy.
3. the formula I compound of claim 1, wherein one of group below the Q representative
Figure A9719843000071
Z wherein 1, Z 2And Z 3Be identical or different, represent hydrogen separately, chlorine, bromine, nitro, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or tert-butyl; CH 2F, CHF 2, CF 3, CH 2Cl, CH 2Br, CHClCH 3Methoxyl group, oxyethyl group, methoxymethyl or ethoxyl methyl, R represents hydrogen, methyl, ethyl, just-or different-propyl group; Methoxymethyl, ethoxyl methyl, just-the propoxy-methyl, just-butoxymethyl; The methyl carbonyl, methyl sulphonyl; Optional separately by the identical or different fluorine that is selected from, chlorine, the substituting group one of methyl or trifluoromethyl or dibasic phenylcarbonyl group or benzyl; Perhaps represent cyclopropyl, X represents oxygen or sulphur, one of following group of Y representative
-CH 2-,-CH(CH 3)-,-CH(C 2H 5)-,-CH(n-C 3H 7)-,CH(i-C 3H 7)-,
-CH 2-CH 2-,-CH (OH)-,-CH (OCH 3)-,-CH (O-CO-CH 3)-,-CH (CN)-,-CHF-,-CHCl-, ,-CH=CH-or-CH 2O-, A (1) representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is: halogen, nitro, cyano group, C 1-C 12-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 12-haloalkyl, C 1-C 4-alkoxyl group has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 2-C 4-alkenyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 2-C 4-halogenated alkenyl, following group Also have phenoxy group, thiophenyl, benzyl oxygen base or pyridyl oxygen base, these groups are optional separately to be selected from one to three replacement of following substituting group by identical or different: halogen, nitro, cyano group, thiocarbamoyl, C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-alkoxy-C 1-C 4-alkyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkylthio, C 1-C 4-alkylthio-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphonyl-C 1-C 4-alkyl, C 1-C 4-alkyl sulphinyl, C 1-C 4-alkyl sulphonyl has for example C of fluorine and chlorine atom of the identical or different halogen atom of 1-5 1-C 4-halogenated alkyl sulfonyl, formyl radical, C 1-C 4-alkyl-carbonyl, C 1-C 4-alkoxy carbonyl, C 1-C 4-alkoxyl group imido grpup-C 1-C 2-alkyl, optional by C 1-C 2One of group that-alkyl-replacement De oxadiazole-3-is basic and following
Figure A9719843000082
(2) the optional cyclopentyl that is replaced by identical or different substituting group one to five of representative, cyclohexyl, cyclopentenyl or cyclohexenyl, possible substituting group is a fluorine, chlorine, bromine, methyl, ethyl, sec.-propyl, methoxyl group or trifluoromethyl,
(3) representative is optional by identical or different substituting group one or dibasic following heterocycle:
Figure A9719843000091
Suitable substituents is under the various situations: fluorine, chlorine, nitro, cyano group; Methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or tert-butyl; Methoxyl group, oxyethyl group, just-or different-propoxy-; Methylthio group;-CF 3,-CHF 2,-CH 2CF 3,-CH 2-CF 2-CHF 2,-CH (CF 3)-CH 3-OCF 3,-OCHF 2, OCH 2CF 3,-O-CH 2-CF 2-CF 3,-OCH 2-CF 2-CHF 2,-O-CH (CF 3)-CH 3-SCF 3Optional separately by identical or different substituting group one or dibasic phenyl, phenoxy group or thiophenyl, possible substituting group is: fluorine, chlorine, nitro, cyano group, methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; R wherein 8Represent C 1-C 4-alkyl, particularly methyl or ethyl; C 1-C 4-alkyl-carbonyl, particularly methyl carbonyl or ethyl carbonyl; And representative is optional by the identical or different C that is selected from 1-C 4-alkyl, particularly methyl or ethyl; Halogen, particularly fluorine or chlorine; C 1-C 4-haloalkyl, particularly trifluoromethyl; C 1-C 4-alkoxyl group, particularly methoxyl group; And C 1-C 4The substituting group one of-halogenated alkoxy, particularly trifluoromethoxy or dibasic phenyl sulfonyl; Or
(4) representative links to each other as required, and optional by identical or different substituting group one below quaternary two-or three cyclic groups:
Figure A9719843000101
Figure A9719843000102
Adamantyl
Figure A9719843000103
Substituting group possible under the various situations is: fluorine, chlorine, bromine, nitro, cyano group; Methyl, ethyl; Methoxyl group, methylthio group, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; R wherein 1Represent hydrogen, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, representative is optional by the identical or different fluorine that is selected from, chlorine, the C that the substituting group one to five of bromine and methyl replaces 3-C 7-cycloalkyl, perhaps representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a fluorine, chlorine, bromine, methyl, ethyl, just-or different-propyl group, methoxy or ethoxy, R 2And R 3Be identical or different, represent hydrogen separately, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl; R 4Represent methylidene, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, representative is optional by the identical or different fluorine that is selected from, chlorine, the substituting group one to five of bromine and methyl replaces the C of (preferred to trisubstituted) 3-C 7-cycloalkyl, perhaps representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a fluorine, chlorine, bromine, methyl, ethyl, just-or different-propyl group, methoxy or ethoxy; Represent oxygen or group=N-OR with W 5With=N-NR 6R 7One of, R wherein 5Represent C 1-C 4-alkyl or representative optional by identical or different substituting group one to trisubstituted benzyl, possible substituting group is a fluorine, chlorine, bromine, nitro, cyano group, trifluoromethyl, trifluoromethoxy, methylthio group, methylsulfinyl, methyl sulphonyl, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxy or ethoxy; And R 6And R 7Be identical or different, represent hydrogen, C separately 1-C 4-alkyl or representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is a fluorine, chlorine, bromine, nitro, cyano group, methyl, ethyl, trifluoromethyl, methoxyl group or trifluoromethoxy.
4. the formula I compound of claim 1, wherein one of group below the Q representative Z wherein 1And Z 2Be identical or different, represent hydrogen separately, chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy, R represents hydrogen, methyl, ethyl, methoxymethyl, ethoxyl methyl, the methyl carbonyl, phenylcarbonyl group or methyl sulphonyl, X are represented oxygen or sulphur, Y representative-CH 2-, A representative optional by identical or different substituting group one to trisubstd phenyl, possible substituting group is: fluorine, chlorine, bromine, nitro, cyano group, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or different-propoxy-, just-, different-, secondary-or tert.-butoxy; Methylthio group, CF 3, OCF 3, OCHF 2, SCF 3, SCCl 2F; CH 2Br, CH 2Cl; Group Also have optional by the identical or different following substituting group one that is selected to trisubstituted phenoxy group: fluorine, chlorine, bromine, nitro, cyano group, thiocarbamoyl, methyl, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or different-propoxy-, just-, different-, secondary-or tert.-butoxy; Methylthio group, methylthiomethyl, CF 3, OCF 3, OCHF 2, SCF 3, SCCl 2F; CH 2Br, CH 2Cl, methoxycarbonyl, methylsulfinyl, methyl sulphonyl, trifluoromethyl sulfonyl or group
Figure A9719843000121
R wherein 1Represent hydrogen, methyl or ethyl; R 2And R 3Be identical or different, represent hydrogen or methyl separately; R 4Represent methylidene or ethyl; Represent oxygen or group=N-OR with W 5, R wherein 5Represent methylidene, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, perhaps representative optional by identical or different substituting group one to trisubstituted benzyl, possible substituting group is to be selected from fluorine, chlorine, bromine, nitro, cyano group, methyl, ethyl, methoxy or ethoxy.
5. the method for the formula I compound of preparation claim 1 is characterised in that
A) in the presence of alkali and in the presence of thinner, make the acyl halide reaction of the aminoisothiazoles and the formula III of formula II, obtain formula (the N-isothiazolyl acid amides of I new replacement a)
Figure A9719843000122
Q wherein, R, Y and A be as above definition separately,
Figure A9719843000123
Wherein Q and R as above definition separately,
Hal-CO-Y-A (III) wherein Y and A as above definition and Hal represent halogen separately; Perhaps
B) if suitably in the presence of thinner, (I is N-isothiazolyl acid amides and sulfuration reagent react a), obtains the N-isothiazolyl thioamides of the new replacement of formula (I b) to make the formula that method (a) obtains Q wherein, R, Y and A be as above definition separately,
Figure A9719843000132
Q wherein, R, Y and A be as above definition separately; Perhaps
C) if suitably in the presence of thinner, make the dithioesters reaction of the aminoisothiazoles and the formula IV of formula II, obtain the N-isothiazolyl thioamides of the new replacement of formula (I b)
Figure A9719843000133
Q wherein, R, Y and A be as above definition separately,
Figure A9719843000141
Wherein Q and R as above definition separately, Wherein as above definition and Alk represent alkyl or group MO-CO-CH separately for Y and A 2-, wherein M represents basic metal (for example sodium or potassium).
6. sterilant is characterised in that, it contains the formula I compound of at least a claim 1.
7. the purposes of the formula I compound pest control of claim 1.
8. the method for pest control is characterised in that, with the formula I compound administration of claim 1 in insect and/or its dried rhizome of rehmannia of dwelling.
9. prepare the method for sterilant, be characterised in that, with the formula I compound of claim 1 with expand agent and/or tensio-active agent and mix.
10. the purposes of the formula I compound sterilant of claim 1.
CN97198430A 1996-07-31 1997-07-18 Substd. N-isothiazolyl-(thio) amides Pending CN1232464A (en)

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