CN1143361A - Phenylthio acetic acid derivatives, process and intermediate products for their production and agents containing them - Google Patents

Phenylthio acetic acid derivatives, process and intermediate products for their production and agents containing them Download PDF

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CN1143361A
CN1143361A CN95191959.8A CN95191959A CN1143361A CN 1143361 A CN1143361 A CN 1143361A CN 95191959 A CN95191959 A CN 95191959A CN 1143361 A CN1143361 A CN 1143361A
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radical
alkylamino
group
alkyl
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H·巴伊尔
H·萨特尔
R·穆勒
W·吉拉米诺斯
A·哈里斯
R·凯斯特恩
F·罗尔
E·阿米尔曼
G·罗恩茨
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BASF SE
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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

Phenylthio acetic acid derivatives of formula (I) in which the components and index have the following meanings: R<1> is hydrogen and alkyl; R<2> is cyano, nitro, trifluoro methyl, halogen, alkyl and alkoxy; m is 0, 1 or 2, in which the radicals R<2> may be different if m is 2; R<3> is hydrogen, cyano, nitro, hydroxy, amino, halogen, alkyl, halogen alkyl, alkoxy, halogen alkoxy, alkylthio, alkylamino or dialkylamino; R<4> is hydrogen, cyano, nitro, hydroxy, amino, halogen, possibly substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, N-alkenyl-N-alkylamino, alkinyl, alkinyloxy, alkinylthio, alkinylamino, N-alkinyl-N-alkylamino, possibly substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, N-cycloalkyl-N-alkylamino, cycloalkenyl, cycloalkenyloxy, cycloalkenylthio, cycloalkenylamino, N-cycloalkenyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N-alkylamino; R<5> is hydrogen, possibly substituted alkyl, cycloalkyl, alkenyl, alkinyl, alkyl carbonyl, alkenyl carbonyl, alkinyl carbonyl or alkyl sulphonyl, possibly substituted aryl, aryl carbonyl, aryl sulphonyl, hetaryl, hetaryl carbonyl or hetaryl sulphonyl. The invention also concern their salts, the process and intermediate products for their production and their use.

Description

Phenylacetic acid derivatives, their preparation and intermediates, and compositions containing them
The invention relates to phenylacetic acid derivatives of formula I and salts thereofWherein the substituents and symbols are as defined below: r1Is hydrogen or C1-C4-an alkyl group; r2Is cyano, nitro, trifluoromethyl, halogen, C1-C4-alkyl or C1
-C4-an alkoxy group; m is 0, 1 or 2, R if m is 22May be different groups; r3Is hydrogen, cyano, nitro, hydroxy, amino, halogen, C1-C4-an alkyl group,
C1-C4-haloalkyl radical, C1-C4-alkoxy radical, C1-C4-halo
Alkoxy radicals, C1-C4Alkylthio radical, C1-C4Alkylamino or bis-
C1-C4-an alkylamino group; r4Is hydrogen, cyano, nitro, hydroxy, amino, halogen, C1-C6-an alkyl group,
C1-C6-alkoxy radical, C1-C6Alkylthio radical, C1-C6Alkyl ammonia
Base, bis-C1-C6-alkylamino radical, C2-C6-alkenyl radical, C2
-C6-alkenyloxy, C2-C6Alkenylthio radical, C2-C6-chain
Alkenylamino, N-C2-C6-alkenyl-N-C1-C6Alkyl ammonia
Base, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6
Alkylenethiol, C2-C6Alkynylamino, N-C2-C6-alkynesradical-N-C1-C6Alkylamino, the hydrocarbon radicals of which may be partially or fully halogenated or carry one to three of the following groups:cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6Alkylamino carbonyl, bis-C1-C6-alkylaminocarbonyl radical, C1-C6Alkylamino thiocarbonyl, bis-C1-C6-alkylaminothiocarbonyl radical, C1-C6-alkylsulfonyl, C1-C6Alkylsulfinyl (C)1-C6-alkylsulfoxyl)，C1-C6-alkoxy radical, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6Alkylthio radical, C1-C6Alkylamino, bis-C1-C6-alkylamino radical, C2-C6Alkenoxy radical, C3-C6-cycloalkyl radical, C3-C6Cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-C4Alkoxy, arylthio, aryl-C1-C4Alkylthio, heteroaryl, heteroaryloxy, heteroaryl-C1-C4Alkoxy, heteroarylthio, heteroaryl-C1-C4Alkylthio, where the cyclic radicals may in turn be partially or fully halogenated and/or carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6Alkyl radical, C1-C6-haloalkyl radical, C1-C6-alkylsulfonyl, C1-C6-alkylsulfinyl radical, C3-C6-cycloalkyl radical, C1-C6-alkoxy radical, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6Alkylthio radical, C1-C6Alkylamino, bis-C1-C6-alkylamino radical, C1-C6Alkylamino carbonyl, bis-C1-C6-alkylaminocarbonyl radical, C1-C6Alkylamino thiocarbonyl, bis-C1-C6-alkylaminothiocarbonyl radical, C2-C6-alkenyl radical, C2-C6-chainAlkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, and C (═ NOR)6)-An-R7；C3-C6-cycloalkyl radical, C3-C6Cycloalkoxy, C3-C6Cycloalkylthio radical, C3-C6Cycloalkylamino, N-C3-C6-cycloalkyl-N-C1-C6-alkylamino radical, C3-C6-cycloalkenyl radical, C3-C6-Cycloalkenyloxy, C3-C6-Cycloalkenylthio group, C3-C6Cycloalkenamides
Radical, N-C3-C6-cycloalkenyl-N-C1-C6-an alkylamino group,
heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-
N-C1-C6Alkylamino, aryl, aryloxy, arylthio, arylamino
Radical, N-aryl-N-C1-C6Alkylamino, heteroaryl, hetero
Aryloxy, heteroarylthio, heteroarylamino, N-heteroaryl-N-C1-
C6Alkylamino, in which the cyclic groups may be partially or fully halogenated or provided with
There are one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino,
carboxy, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl radical, C1
-C6-haloalkyl radical, C1-C6-alkylsulfonyl, C1-C6-
Alkylsulfinyl radical, C3-C6-cycloalkyl radical, C1-C6-an alkoxy group,
C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6
Alkylthio radical, C1-C6Alkylamino, bis-C1-C6-alkanesAn amino group as a radical,
C1-C6alkylamino carbonyl, bis-C1-C6-an alkyl-amino-carbonyl group,
C1-C6alkylamino thiocarbonyl, bis-C1-C6Alkyl amino sulfur
Substituted carbonyl group, C2-C6-alkenyl radical, C2-C6-an alkenyloxy group, a benzyl group,
benzyloxy, aryl, aryloxy, heteroaryl and heteroaryloxy; r5Is a hydrogen atom, and is,
C1-C10-alkyl radical, C3-C6-cycloalkyl radical, C2-C10-alkenes
Base, C2-C10-alkynyl, C1-C10-alkylcarbonyl group, C2-C10
-alkenylcarbonyl radical, C3-C10Alkynylcarbonyl or C1-C10-alkyl sulfonic acid
Acyl radicals which may be partially or fully halogenated or carry one to three of the following
Group (b): cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl,
aminothiocarbonyl, halogen, C1-C6-alkyl radical, C1-C6-halo
Alkyl radical, C1-C6-alkylsulfonyl, C1-C6-alkylsulfinyl
Base, C1-C6-alkoxy radical, C1-C6-haloalkoxy, C1-
C6-alkoxycarbonyl, C1-C6Alkylthio radical, C1-C6-an alkylamino group,
bis-C1-C6-alkylamino radical, C1-C6Alkylamino carbonyl, bis-
C1-C6-alkylaminocarbonyl radical, C1-C6-an alkylamino-thiocarbonyl group,
bis-C1-C6-alkanesAminothiocarbonyl radical, C2-C6-an alkenyl group,
C2-C6-alkenyloxy, C3-C6-cycloalkyl radical, C3-C6-Ring
Alkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy
Aryl, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, and combinations thereof
In which the cyclic groups may in turn be partially or fully halogenated or carry one to three radicals
The following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl,
aminothiocarbonyl, halogen, C1-C6-alkyl radical, C1-C6-halo
Alkyl radical, C1-C6-alkylsulfonyl, C1-C6-an alkylsulfinyl group,
C3-C6-cycloalkyl radical, C1-C6-alkoxy radical, C1-C6-halo
Alkoxy radical, C1-C6-alkoxycarbonyl, C1-C6Alkylthio radical, C1
-C6Alkylamino, bis-C1-C6-alkylamino radical, C1-C6-alkanes
Aminocarbonyl, bis-C1-C6-alkylaminocarbonyl radical, C1-C6-alkanes
Aminothiocarbonyl, bis-C1-C6-alkylaminothiocarbonyl radical, C2
-C6-alkenyl radical, C2-C6-alkenyloxy, benzyl, benzyloxy,
aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio,
or C (═ NOR)6)-An-R7；
Aryl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylcarbonyl or hetaryl
Alkylsulfonyl radicals, which may be partially or fully halogenated or carry one to three
The following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, amino
Carbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl radical, C1-C6
-haloalkyl radical, C1-C6-alkylcarbonyl group, C1-C6-alkylsulfonyl
Base, C1-C6-alkylsulfinyl radical, C3-C6-cycloalkyl radical, C1-C6
-alkoxy radical, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1
-C6Alkylthio radical, C1-C6Alkylamino, bis-C1-C6-an alkylamino group,
C1-C6alkylamino carbonyl, bis-C1-C6-alkylaminocarbonyl radical, C1
-C6Alkylamino thiocarbonyl, bis-C1-C6-an alkylaminothiocarbonyl group,
C2-C6alkenyl radical, C2-C6Alkenyloxy, benzyl, benzyloxy, aryl,
aryloxy, heteroaryl, heteroaryloxy or C (═ NOR)6)-An-R7(ii) a Wherein A is oxygen, sulfur or nitrogen, wherein the nitrogen carries hydrogen or C1-C6An alkyl group;n is 0 or 1; r6Is hydrogen or C1-C6-alkyl, and R7Is hydrogen or C1-C6-an alkyl group.
The invention also relates to processes and intermediates for preparing these compounds and to compositions containing them for controlling animal pests and harmful fungi.
The control of pests by phenylacetic acid derivatives has been disclosed in the literature (EP-A432503, EP-A463488).
It is an object of the present invention to provide novel compounds having higher activity.
We have found that this object is achieved by the phenylacetic acid derivatives defined at the outset. We have also found processes and intermediates for their preparation, and also compositions containing them for controlling animal pests and harmful fungi and their use.
The compounds I can be obtained by methods known in the literature.
Essentially, the radical- (NOCH) is formed first3)-COSR1Or first form a group-CH2ON＝(CR3)-C(R4)＝NOR5It is not critical in the synthesis of compound I.
Group- (NOCH)3)-COSR1The syntheses of which are disclosed, for example, in the literature cited at the outset.
Side chain-CH2ON＝C(R3)-C(R4)＝NOR5The mode of synthesis of (A) is mainly dependent on the substituent R3And R4The nature of (c). 1. If R is3And R4Not being halogen, the radical-CH2ON＝C(R3)-C(R4)＝NOR5
Generally from benzyl derivatives of the general formula II with hydroxy groups of the formula III
The reaction of the imide is complete.In the formula II, L1Is a leaving group which can be nucleophilically substituted, for example a halogen or a sulfonate group, preferably a chloride, bromide, iodide, mesylate, tosylate or triflate group. The reaction is carried out in a manner known per se in the inert organic solvent in the presence of a base, such as sodium hydride, potassium hydroxide, potassium carbonate and triethylamine, in a manner described by Houben-Weyl, Vol.E 14b, p.370ff and Houben-Weyl, Vol.10/1, p.1189ff. The desired hydroxyimine III can be obtained, for example, by reaction of the corresponding dihydroxyimine IV with a nucleophilic substitution reagent VI to give R5-L2+ HON＝C(R4)-C(R3)＝NOH VI IV
→ R5-ON＝C(R4)-C(R3)＝NOH
III
L in the formula VI2Being a leaving group which can be nucleophilically substituted, e.g. halogen or sulfonic acid
An ester group, preferably a chloride, bromide, iodide, mesylate, tosylate or tris
A fluoromethanesulfonate group.
The reaction is carried out as described by Houben-Weyl, Vol.E 14b, p.307ff, p.370ff and
p.385ff; Houben-Weyl, Vol.10/4, p.55ff, p.180ff and p.217ff;
Houben-Weyl, Vol. E5, p780 ff. Said process being carried out in the presence of a base (e.g. carbon)
Potassium, potassium hydroxide, sodium hydride, pyridine and triethylamine) in the presence of an inert gas
In organic solvents, in a manner known per se. 1.1 optionally, the compounds I can also be derivatized by first using a dihydroxyimine
Substance IV converts the benzyl derivative II into the corresponding benzyl oxime of formula V, which is then reacted with
Figure A9519195900161
The reaction can be carried out as described by Houben-Wey1, Vol.10/1, p.1189ff; houben-
Weyl, Vol.E 14b, p.307ff, p.370ff and p.385ff; houben-
Weyl, Vol.10/4, p.55ff, p.180ff and p.217ff; the number of Houben-Weyl,
Vol.E5, p.780ff. The method is carried out in the presence of a base (such as potassium carbonate, hydrogen and oxygen)
Potassium hydride, sodium hydride, pyridine or triethylamine) in the presence of an inert organic solvent
In a solvent in a manner known per se. 1.2 can also be prepared in a similar manner by reaction with hydroxylamine IXa or its salt IXb
The desired hydroxyimine of the formula III is prepared from a carbonylhydroxyimine VII.
→ R5-ON＝C(R4)-C(R3)＝NOH
III
Q in the formula IXb-Being anions of acids, especially mineral acids, e.g. halides
And (ii) ions such as chloride ions. The reaction can be carried out as described in EP-A513580;
Houben-Weyl，Vol.19/4，p.73ff；Houben-Weyl，Vol.E
14b, p.369ff and p.385ff in an inert organic solvent,
in a manner known per se. 1.3 optionally, the compounds I can also be prepared by first using carbonylhydroxyimine derivatives
VII conversion of the benzyl derivative II into the corresponding benzyloxyimine of the formula VIII,
and then reacting VIII with hydroxylamine IXa or a salt thereof IXb.
Figure A9519195900171
The reaction was carried out as Houben-Weyl, Vol.E14b, p369ff, Houben-
Weyl, Vol.10/1, p.1189ff and Houben-Weyl, Vol.10/4,
p.73ff or EP-A513580 in an inert organic solvent
In a manner known per se. 1.4 Another possible process for preparing the compounds I is the reaction of benzyl derivatives II with N
-hydroxyphthalimide reaction and subsequent hydrazinolysis to benzylhydroxylamine IIa,
and IIa is further reacted with a carbonyl compound X.
Figure A9519195900181
R5-ON＝C(R4)-C(R3)＝O + IIa → I
The reaction can be carried out in a manner known per se in inert organic solvents in accordance with the methods described in EP-A463488, DE-A4228867.3. The desired carbonyl compounds X can be prepared, for example, as follows: by means ofReacting the hydroxyiminocarbonyl compound VIIb with a nucleophilic substitution reagent VI
VI VIIb X or by reaction of the corresponding dicarbonyl compound XI with hydroxylamine IXa or its salts IXb
→ R5-ON＝C(R4)-C(R3)＝O
X
These reactions can be carried out according to EP-A513580, Houben-Weyl, Vol.
10/4, p.55ff, p.73ff, p.180ff and p.217ff, Houben-Weyl,
vol.E 14b, p.307ff and 369ff, Houben-Weyl,
Vol.E5, p.780ff. The process described, in an inert organic solvent, to
In a manner known per se. 1.5 correspondingly, the above-mentioned compounds I can also be prepared by first using the hydroxyiminocarbonyl group
VIIb conversion of benzylhydroxylamine IIa to the corresponding benzyloxyimine derivative of formula V
And then reacting V with a nucleophilic substitution reagent VI.1.6 analogously, the above-mentioned compounds I can also be derived by first using dicarbonyl of the formula XI
Biologically converting benzylhydroxylamine IIa to the benzyloxyimine derivative VIII, and then
VIII and hydroxylamine IXa or its salt IXb reaction to get.
Figure A9519195900192
Figure A9519195900201
2. Wherein R is3And/or R6The compounds which are halogen atoms can be prepared by methods known per se,
From the corresponding precursor in which the relevant group is a hydroxyl group (cf. houben-Weyl,
Vol.E5，p.631；J.Org.Chem.36(1971)，233；J.Org.
chem.57(1992), 3245). Preferably, corresponding to give halogenderivatives
The reaction is completed in steps I and VIII. 3. Wherein R is3And/or R4Conjugation to molecular Structure by O, S or N
The compounds can be prepared by methods known per se from the corresponding radicals in which the radicals concerned are halogen atoms
The precursors were obtained (cf. Houben-Weyl, Vol. E5, p.826ff and 128ff,
J.Org.Chem.36(1971)，233，J.Org.Chem.46(1981)，
3623). Preferably, the corresponding conversion of the halogen derivative is carried out in steps I and VIII
To complete the process. 4. Wherein R is3And R4Compounds attached to the molecule via an oxygen atom may sometimes also be present
Obtained by methods known per se from the corresponding precursors whose relevant groups are hydroxyl groups
(cf.Houben-Weyl，Vol.E5，p.826-829，Aust.J.Chem.27
(1974),1341-9). Preferably, corresponding reactions leading to alkoxy derivatives
In steps I and VIII. 5. Wherein R is3Compounds other than halogen are preferably prepared by first reacting compounds according to EP-A493711, which converts compound X to the corresponding benzoic acid XIII using the lactone XII and converts XIII to the cyanocarboxylic acid XIV via the corresponding acid halide, which is converted to the α -keto ester XV by the method of the Pinner reaction (Angew. chem.94(1982), 1), the thioester obtained by the "transesterification" of the derivative XV, which is subsequently converted to compound I.
Figure A9519195900221
6. In a further preparation process, the compounds I can alsobe prepared, for example, from the compounds XV by first converting the keto group into the oxime ether and then converting the ester function into the corresponding thioester via carboxylic acid or directly or by activation, for example by formation of an acid chloride [ Organikum, 16 th edition (1985), pp.415, 423 and 622].
Figure A9519195900222
The compounds II can be prepared by the processes described in EP-A432503, EP-A463488, EP-A386-561.
Having C ═ C and C ═ N double bonds, E/Z isomer mixtures can be obtained in the course of the preparation, which can be isolated as the mono-pure compounds by customary methods, for example crystallization and chromatography.
However, the isomer mixtures obtained in the synthesis do not necessarily need to be separated, since the individual isomers can in some cases be interconverted during the preparation or during the application (for example under the action of light, acids or bases). Corresponding transformations can also take place after application, for example in the plant treatment phase on the treated plants or in the controlled harmful fungi or animal pests.
For the C ═ X double bonds, the E isomers of compound I (depending on-OCH) are preferred in view of their activity3and-COSR1Mutual position of radicals)
for-C (R)3)＝NOCH2Double bonds, preference being given to the cis-isomers of the compounds I (depending on R) in view of their activity3and-OCH2-mutual position of the radicals)
The collective terms used in the definition of compound 3 given above generally denote the following groups:halogen:fluorine, chlorine, bromine and iodine;alkyl groups:straight-chain or branched alkyl radicals having 1 to 4, 6or 10 carbon atoms, e.g. C1-C6Alkyl radicals such as the methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3-dimethylbutyl, 1-ethylbutyl, 2-dimethylbutyl, 3-dimethylbutyl, 2-ethylbutyl, 1, 2-trimethylpropyl, 1, 2, 2-trisMethyl radicalPropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;alkylamino group:an amino group having a branched or branched alkyl group having 1 to 6 carbon atoms as described above;a bisalkylamino group:an amino group having two linear or branched alkyl groups having 1 to 6 carbon atoms as described above independently of each other;an alkylcarbonyl group:a straight or branched alkyl group of 1 to 10 carbon atoms attached to the main structure through a carbonyl (-CO-);an alkylsulfonyl group:via sulfonyl group (-SO)2-) a straight or branched alkyl group of 1 to 6 or 10 carbon atoms attached to the main structure;alkylsulfinyl group:straight or branched chain alkyl of 1 to 6 carbon atoms attached to the main structure through sulfinyl (-O) -);an alkylamino carbonyl group:the above alkylamino group having 1 to 6 carbon atoms bonded to the main structure via a carbonyl group (-CO-);bis-alkylaminocarbonyl:the bisalkylamino groups depicted above attached to the main structure through a carbonyl (-CO-) group wherein each alkyl group has from 1 to 6 carbon atoms;alkylamino thiocarbonyl:the above alkylamino group having 1 to 6 carbon atoms which is attached to the main structure via a thiocarbonyl (-CS-).Bis-alkylamino-thiocarbonyl:the above-described bisalkylamino groups attached to the main structure via a thiocarbonyl (-CS-) group wherein each alkyl group has 1 to 6 carbon atoms;halogenated alkyl groups:straight-chain or branched alkyl radicals having 1 to 6 carbon atoms, the hydrogen atoms of which may be partially or fully substituted by halogen atoms as defined above, e.g. C1-C2Haloalkyl groups such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl and pentafluoroethyl; alkoxy groups: straight or branched chain alkyl radicals as defined above having 1 to 4 or 6 carbon atoms, e.g. C, attached to the main structure via an oxygen atom (-O-)1-C6Alkoxy radicals, e.g. methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropylOxy, 2-methylpropoxy, 1-dimethylethoxy, pentyloxy, 1-methylButoxy, 2-methylbutoxy, 3-methylbutoxy, 2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1, 1-dimethylbutyloxy, 1, 2-dimethylbutyloxy, 1, 3-dimethylbutyloxy, 2, 2-dimethylbutyloxy, 2, 3-dimethylbutyloxy, 3-dimethylbutyloxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 2-trimethylpropoxy, 1, 2, 2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;an alkoxycarbonyl group:a straight or branched alkyl group having 1 to 6 carbon atoms which is attached to the main structure through an oxycarbonyl group (-O (C ═ O) -);haloalkoxy groups:straight or branched alkyl of 1 to 6 carbon atoms which is attached to the main structure through an oxygen atom, the hydrogen atoms of which may be partially or fully substituted by halogen atoms as described above;alkylthio group:straight-chain or branched alkyl radicals as defined above having 1 to 4 or 6 carbon atoms, e.g. C, attached to the main structure viaa sulfur atom (-S-)1-C6Alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylethylthio, 3-methylbutylthio, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1-dimethylbutylthio, mesityl, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2-dimethylbutylthio, 2, 3-dimethylbutylthio, 1-dimethylbutylthio, 2, 3-dimethylbutylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 3, 3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 2-trimethylpropylthio, 1, 2, 2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;cycloalkyl groups:monocycloalkyl radicals having 3 to 6 ring carbon atoms, e.g. cyclopropyl, cyclobutylAlkyl, cyclopentyl and cyclohexyl; alkenyl: straight-chain or branched alkenyl having 2 to 6 or 10 carbon atoms, the double bond being in any position, e.g. C2-C6Alkenyl radicals, e.g. vinyl1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 2-methyl-3-butenyl, 2-butenyl, 3-methyl-2-butenyl, 2-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 1-methyl-hexenyl, 1-hexenyl,2-methyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1-dimethyl-2-butenyl, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1-methyl-3-pentenyl, 3-methyl-3-pentenyl, 3-methyl-pentenyl, 4-methyl-pentenyl, 1-dimethyl-2-butenyl, 1, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-3-butenyl, 2-dimethyl-3-butenyl, 2, 3-dimethyl-1-butenyl, 2, 3-dimethyl-2-butenyl, 2, 3-dimethyl-3-butenyl, 3-dimethyl-1-butenyl, 3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 2-dimethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl, 2-ethyl-3-butenyl,1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;alkenyloxy:straight or branched chain alkenyl having 2 to 6 carbon atoms, the double bond of which may be in any position, attached to the main structure through an oxygen atom (-O-);an alkenylcarbonyl group:straight or branched chain alkenyl having 2 to 10 carbon atoms, the double bond of which may be in any position, attached to the main structure via a carbonyl group (-CO-);alkenylthio or alkenylamino:straight or branched alkenyl having 2 or 6 carbon atoms, the double bond of which may be in any position, attached to the main structure through a sulfur atom (alkenylthio) or a nitrogen atom (alkenylamino);alkynyl:straight-chain or branched alkinyl with 2 to 10 carbon atoms, the triple bond being in any position, e.g. C2-C6Alkynyl, such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1-dimethyl-2-butynyl, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;alkynylcarbonyl:a straight or branched chain alkynyl group having 3 to 10 carbon atoms, having a triple bond at any position, linked to the main structure via a carbonyl group (-CO-);alkynyloxy or alkynylthio and alkynylamino:straight or branched chain alkynyl having 2 to 6 carbon atoms with triple bonds in any position, connected to the main structure via an oxygen atom (alkynyloxy) or a sulfur atom (alkynylthio) or a nitrogen atom (alkynylamino);cycloalkoxy or cycloalkylthio and cycloalkylamino:via an oxygen atom (cycloalkoxy) or a sulfur atomA monocycloalkyl group having 3 to 6 ring carbon atoms with the atom (cycloalkylthio) or nitrogen (cycloalkylamino) attached to the main structure, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl;cycloalkenyl or cycloalkenyloxy, cycloalkenylthio and cycloalkenylamino:a monocyclic alkenyl group having 3 to 6 ring carbon atoms which is bonded to the main structure directly or via an oxygen atom (cycloalkenyloxy) or a sulfur atom (cycloalkenylthio) or a nitrogen atom (cycloalkenylamino), for example cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl;heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclylamino:directly or via an oxygen atom (heterocyclyloxy) or via a sulfur atom (heterocyclylthio)Or a three-to six-membered saturated or partially unsaturated monocyclic or polycyclic heterocycle containing one to three heteroatoms selected from oxygen, nitrogen and sulfur, which is attached to the main structure via a nitrogen atom (heterocycloamino group), such as 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1, 2, 4-oxadiazolidin-3-yl, 1, 2, 4-oxadiazolidin-5-yl, 1, 2, 4-thiadiazolidin-3-yl, 1, 2, 4-thiadiazolidin-5-yl, 1, 2, 4-triazolidin-3-yl, 1, 3, 4-oxadiazolidin-2-yl, 1, 3, 4-thiadiazolidin-2-yl, 1, 3, 4-triazolidin-2-yl, 2, 3-dihydrofuran-3-yl, 2, 3-dihydrofuran-4-yl, 2, 3-dihydrofuran-5-yl, 2, 5-dihydrofuran-2-yl, 2, 5-dihydrofuran-3-yl, 2, 3-dihydrothien-2-yl, 2, 3-dihydrothien-3-yl, 2, 3-dihydrothien-4-yl, 2, 3-dihydrothien-5-yl, 2, 5-dihydrothien-2-yl, 2, 5-dihydrothien-3-yl, 2, 3-dihydropyrrol-2-yl, 2, 3-dihydropyrrol-3-yl, 2, 3-dihydropyrrol-4-yl, 2, 3-dihydropyrrol-5-yl, 2, 5-dihydropyrrol-2-A group, 2, 5-dihydropyrrol-3-yl, 2, 3-dihydroisoxazol-4-yl, 2, 3-dihydroisoxazol-5-yl, 4, 5-dihydroisoxazol-3-yl, 4, 5-dihydroisoxazol-4-yl, 4, 5-dihydroisoxazol-5-yl, 2, 5-dihydroisothiazol-3-yl, 2, 5-dihydroisothiazol-4-yl, 2, 5-dihydroisothiazol-5-yl, 2, 3-dihydroisopyrazol-3-yl, 2, 3-dihydroisopyrazol-4-yl, 2, 3-dihydroisopyrazol-5-yl, 4, 5-dihydroisopyrazol-3-yl, 4, 5-dihydroisopyrazol-4-yl, 4, 5-dihydroisopyrazol-5-yl, 2, 5-dihydroisopyrazol-3-yl, 2, 5-dihydroisopyrazol-4-yl, 2, 5-dihydroisopyrazol-5-yl, 2, 3-dihydrooxazol-3-yl, 2, 3-dihydrooxazol-4-yl, 2, 3-dihydrooxazol-5-yl, 4, 5-dihydrooxazol-3-yl, 4, 5-dihydrooxazol-4-yl, 4, 5-di-isoxazol-4-ylOxazol-5-yl, 2, 5-dihydrooxazol-3-yl, 2, 5-dihydrooxazol-4-yl, 2, 5-dihydrooxazol-5-yl, 2, 3-dihydrothiazol-2-yl, 2, 3-dihydrothiazol-4-yl, 2, 3-dihydrothiazol-5-yl, 4, 5-dihydrothiazol-2-yl, 4, 5-dihydrothiazol-4-yl, 4, 5-dihydrothiazol-5-yl, 2, 5-dihydrothiazol-2-yl, 2, 5-dihydrothiazol-4-yl, 2, 5-dihydrothiazol-5-yl, 2, 3-dihydroimidazol-2-yl, 2, 3-dihydroimidazol-4-yl, 2, 3-dihydroimidazol-5-yl, 4, 5-dihydroimidazol-2-yl, 4, 5-dihydroimidazol-4-yl, 4, 5-dihydroimidazol-5-yl, 2, 5-dihydroimidazol-2-yl, 2, 5-dihydroimidazol-4-yl, 2, 5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1, 3, 5-tetrahydrotriazin-2-yl, 1, 2, 4-tetrahydrotriazin-3-yl, 1, 3-dihydrooxazin-2-yl, 1, 3-dithian-2-yl, 2-tetrahydropyranyl, 1, 3-dioxan-2-yl, 2, 4, 5, 6-tetrahydropyridin-2-yl, 4H-1, 3-thiazin-2-yl, 4H-3, 1-benzothiazin-2-yl,1, 1-dioxo-2, 3, 4, 5-tetrahydrothiophen-2-yl, 2H-1, 4-benzothiazin-3-yl, 2H-1, 4-benzoxazin-3-yl, 1, 3-dihydrooxazin-2-yl, 1, 3-dithian-2-yl;aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl:directly or via oxygen atom (-O-) (aryloxy) or sulfur atom (-S-) (arylthio), via carbonyl (-CO-) (arylcarbonyl) or sulfonyl (-SO)2- (arylsulfonyl) an aromatic monocyclic or polycyclic hydrocarbon group bonded to the main structure, such as phenyl, naphthyl and phenanthryl or phenoxy, naphthoxy and phenanthroxy and the corresponding carbonyl and sulfonyl groups;arylamino group:an aromatic monocyclic or polycyclic hydrocarbon group bonded to the main structure through a nitrogen atom;heteroaryl or heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylsulfonyl:directly or via oxygen atom (-O-) (heteroaryloxy) or sulfur atom (-S-) (heteroarylthio), via carbonyl (-CO-) (heteroarylcarbonyl) or sulfonyl (-SO-)2- (Heteroarylsulfonyl) attached to the main structure and containing, in addition to carbon atoms, one to four nitrogen atoms, or one to three nitrogen atoms and an oxygen or sulfur atom, or an aromatic monocyclic ring containing one oxygen atom or one sulfur atomPolycyclic radicals, e.g. derivatives ofA 5-membered heteroaryl group containing one to three nitrogen atoms:containing one to three atoms other than carbon atoms
5-membered ring heteroaryl of a ring nitrogen atom, such as 2-pyrrolyl, 3-pyrrolyl,
3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-
Imidazolyl, 1, 2, 4-triazol-3-yl and 1, 3, 4-triazol-
2-yl; -Containing one to four nitrogen atoms, or one to three nitrogen atoms and one sulfur or oxygen atom,
or a 5-membered heteroaryl group containing one sulfur or one oxygen atom:in addition to carbon atoms, may be
Containing one to four nitrogen atoms, or one to three nitrogen atoms and one sulfur or oxygen atom,
Or 5-membered ring heteroaryl containing one sulfur or one oxygen atom as ring member, e.g. 2
-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyranyl
Pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl
Oxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3
-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl
Azolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl
Radical, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazole-3-
1, 2, 4-oxadiazole-5-yl, 1, 2, 4-thiadiazole-
3-yl, 1, 2, 4-thiadiazol-5-yl, 1, 2, 4-triazole
-3-yl, 1, 3, 4-oxadiazol-2-yl, 1, 3, 4-thia
Oxadiazol-2-yl, 1, 3, 4-triazol-2-yl; -Containing one to three nitrogen atoms or containing one nitrogen atom and/or one oxygen or sulfur atom
5-membered heteroaryl fused with benzene:containing one to four nitrogen atoms in addition to carbon atoms
Atoms, or one to three nitrogen atoms and one sulfur or oxygen atom, or one oxygen or one
5-membered ring heteroaryl of a ring atom with a sulfur atom, wherein two adjacent ring carbon atoms
The ring, or one ring nitrogen atom and an adjacent ring carbon atom, may be replaced by butane-1, 3-bis
Alkene-1, 4-diyl bridges. -5-membered heteroaryl groups containing one to four nitrogen atoms, bound via a nitrogen atom, or via a nitrogen atom
A 5-membered heteroaryl group fused to a benzene ring containing one to three nitrogen atoms attached:removing device
Rings containing, in addition to carbon atoms, from one to four nitrogen atoms, or from one to three nitrogen atoms
An atomic 5-membered ring heteroaryl group in which two adjacent ring carbon atoms or one ring nitrogen
The atoms and adjacent ring carbon atoms may be replaced by but-1, 3-diene-1, 4-bis
Radical bridges, which are attached to the main structure through a ring nitrogen atom; -6-membered heteroaryl containing one to three or one to four nitrogen atoms:in addition to the carbon atoms,
6-membered ring heteroaryl groups which may contain one to three or one to four ring nitrogen atoms, e.g.
2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-
Pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl
1, 3, 5-triazin-2-yl, 1, 2, 4-triazin-3-
1, 2, 4, 5-tetrazin-3-yl; -A 6-membered heteroaryl group containing one to four nitrogen atoms fused to a benzene ring:two adjacent
6-membered rings whose ring carbon atoms can be bridged by but-1, 3-diene-1, 4-diyl
Ring heteroaryl groups such as quinoline, isoquinoline, quinazoline, and quinoxaline; or the corresponding oxy,thio, carbonyl or sulfonyl group;a heteroaromatic amino group:aromatic hydrocarbons containing, in addition to the ring carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom, bound to the main structure via a nitrogen atomMonocyclic or polycyclic groups.
"partially or fully halogenated" means that the hydrogen atoms in a defined group are partially or fully substituted by the same or different halogen atoms described above.
In view of their biological activity, preference is given to compounds of the formula I in which m is 0.
Also preferred is the case where R1A compound of formula I which is methyl.
In addition, preferred is the case where R is3Compound I which is hydrogen, hydroxy, cyclopropyl, chloro, methyl, ethyl, 1-methylethyl, methoxy, methylthio or phenyl.
In addition, preferred is the case where R is3Compound I being methyl.
In addition, preferred is the case where R is3Compound I which is methoxy.
In addition, preferred is the case where R is3Compound I being a hydroxyl group.
In addition, preferred is the case where R is3Compound I which is chloro.
In addition, preferred is the case where R is4Compounds I which are hydrogen, hydroxy, cyclopropyl, chloro, methyl, ethyl, isopropyl, methoxy and methylthio.
In addition, preferred is the case where R is4Compound I being methyl.
In addition, preferred is the case where R is4Compound I which is methoxy.
In addition, preferred is the case where R is4Compound I being a hydroxyl group.
In addition, preferred is the case where R is4Compound I being ethyl.
In addition, preferred is the case where R is4Compound I which is isopropyl.
In addition, preferred is the case where R is4Compound I which is cyclopropyl.
In addition, R is preferably wherein4Compound I being an aryl or heteroaryl group.
In addition, R is preferably wherein4Compound I being phenyl.
In addition, preferred is the case where R is5Compound I being methyl or ethyl.
In addition, preferred is the case where R is5Is aralkyl or heteroarylAlkyl compounds I.
In addition, preferred is the case where R is5Compound I which is an aryloxyalkyl or heteroaryloxyalkyl.
In addition, preferred is the case where R is4Compound I which is unsubstituted or substituted aryl or heteroaryl.
In addition, preferred is the case where R is4Compound I which is unsubstituted or substituted pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl.
In addition, preferred is the case where R is4Is unsubstituted or substituted furyl, thienyl or pyranylPyrrole-based compounds I.
In addition, preferred is the case where R is4Compound I which is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
In addition, preferred is the case where R is4Compound I which is an unsubstituted or substituted oxadiazolyl, thiadiazolyl or triazolyl group.
In addition, preferred is the case where R is4Is unsubstituted or substituted by one or more radicals selected from nitro, cyano, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, halogen, C1-C4Alkyl radical, C1-C4Haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4Alkylamino, bis-C1-C4-alkylamino radical, C1-C4-alkylsulfonyl, C1-C4-alkoxycarbonyl, C1-C4An alkylaminocarbonyl group or a bis-C1-C4-phenyl substituted by 1 or 2 groups of alkylaminocarbonyl.
In addition, preferred is the case where R is5Compound I being an aryl or heteroaryl group.
In view of their use, particular preference is given to the compounds I compiled in the following table. TABLE 1
A compound of the general formula I.1, wherein (R)2)mBeing hydrogen, the substituent R in each compound3、R4And R5Corresponds to a row in table a.
Figure A9519195900331
TABLE 2
A compound of the general formula I.1, wherein (R)2)mBeing chlorine, the substituent R in each compound3、R4And R5Corresponds to a row in table a.
TABLE A
No. R3 R4 R5
1 CH3 CH3 H
2 CH3 CH3 CH3
3 CH3 CH3 C2H5
4 CH3 CH3 n-C3H7
5 CH3 CH3 i-C3H7
6 CH3 CH3 Cyclopropyl group
7 CH3 CH3 n-C4H9
8 CH3 CH3 s-C4H9
9 CH3 CH3 i-C4H9
10 CH3 CH3 t-C4H9
11 CH3 CH3 n-C5H11
12 CH3 CH3 i-C5H11
13 CH3 CH3 novel-C5H11
14 CH3 CH3 Cyclopentyl group
15 CH3 CH3 n-C6H13
16 CH3 CH3 Cyclohexyl radical
17 CH3 CH3 n-C8H17
18 CH3 CH3 CH2CH2Cl
19 CH3 CH3 (CH2)4Cl
20 CH3 CH3 CH2CN
21 CH3 CH3 CH2CH2CN
22 CH3 CH3 (CH2)3CN
23 CH3 CH3 (CH2)4CN
24 CH3 CH3 (CH2)6CN
25 CH3 CH3 Cyclohexyl methyl radical
26 CH3 CH3 2-Cyclohexyleth-1-yl
27 CH3 CH3 Cyclopropyl methyl group
28 CH3 CH3 2-Cyclopropyleth-1-yl
29 CH3 CH3 2-methoxyethyl-1-yl
30 CH3 CH3 2-ethoxyeth-1-yl
31 CH3 CH3 2-Isopropoxyethyl-1-yl
32 CH3 CH3 3-methoxyprop-1-yl
33 CH3 CH3 3-ethoxypropan-1-yl
34 CH3 CH3 3-Isopropoxyprop-1-yl
35 CH3 CH3 4-Methoxybutan-1-yl
36 CH3 CH3 4-Isopropoxybutan-1-yl
No. R3 R4 R5
37 CH3 CH3 3-propenyl group
38 CH3 CH3 But-2-en-1-yl
39 CH3 CH3 3-methylbut-2-en-1-yl
40 CH3 CH3 2-vinyloxyethyl-1-yl group
41 CH3 CH3 Allyloxyeth-1-yl
42 CH3 CH3 2-trifluoromethoxyeth-1-yl
43 CH3 CH3 3-Trifluoromethoxypropan-1-yl
44 CH3 CH3 4-Difluoromethoxybutan-1-yl
45 CH3 CH3 Hydroxycarbonylmethyl radical
46 CH3 CH3 Methoxycarbonyl methyl group
47 CH3 CH3 Aminocarbonylmethyl group
48 CH3 CH3 Methylaminocarbonylmethyl group
49 CH3 CH3 N, N-dimethylaminocarbonylmethyl
50 CH3 CH3 2-hydroxycarbonyleth-1-yl
51 CH3 CH3 2-methoxycarbonyleth-1-yl
52 CH3 CH3 2-aminocarbonyleth-1-yl
53 CH3 CH3 2-methylaminocarbonyleth-1-yl
54 CH3 CH3 2-dimethylaminocarbonyl-1-ethyl
55 CH3 CH3 2-aminoeth-1-yl
56 CH3 CH3 2-Aminoprop-1-yl
57 CH3 CH3 4-Aminobut-1-yl
58 CH3 CH3 3-dimethylaminoprop-1-yl
59 CH3 CH3 4-aminothiocarbonylbut-1-yl
60 CH3 CH3 2-oxopropyl radical
61 CH3 CH3 Cyclohexyl radical
62 CH3 CH3 Cyclopropyl group
63 CH3 CH3 Cyclopentyl group
64 CH3 CH3 2-Methoxyiminopropan-1-yl
65 CH3 CH3 2-Methoxyiminoeth-1-yl
66 CH3 CH3 6-aminocarbonylhex-1-yl
67 CH3 CH3 3-aminothiocarbonylpropan-1-yl
68 CH3 CH3 2-aminothiocarbonyleth-1-yl
69 CH3 CH3 Aminothiocarbonylmethyl group
70 CH3 CH3 4- (N, N-dimethylamino) But-1-yl
71 CH3 CH3 2- (methylthio) eth-1-yl
72 CH3 CH3 2- (methylsulfonyl) eth-1-yl
No. R3 R4 R5
73 CH3 CH3 4- (methylthio) propan-1-yl
74 CH3 CH3 4- (methylsulfonyl) propan-1-yl
75 CH3 CH3 Benzyl radical
76 CH3 CH3 2-F-C6H4-CH2
77 CH3 CH3 3-F-C6H4-CH2
78 CH3 CH3 4-F-C6H4-CH2
79 CH3 CH3 2，3-F2-C6H3-CH2
80 CH3 CH3 2，4-F2-C6H3-CH2
81 CH3 CH3 2，5-F2-C6H3-CH2
82 CH3 CH3 2，6-F2-C6H3-CH2
83 CH3 CH3 3，4-F2-C6H3-CH2
84 CH3 CH3 3，5-F2-C6H3-CH2
85 CH3 CH3 2-Cl-C6H4-CH2
86 CH3 CH3 3-Cl-C6H4-CH2
87 CH3 CH3 4-Cl-C6H4-CH2
88 CH3 CH3 2，3-Cl2-C6H3-CH2
89 CH3 CH3 2，4-Cl2-C6H3-CH2
90 CH3 CH3 2，5-Cl2-C6H3-CH2
91 CH3 CH3 2，6-Cl2-C6H3-CH2
92 CH3 CH3 3，4-Cl2-C6H3-CH2
93 CH3 CH3 3，5-Cl2-C6H3-CH2
94 CH3 CH3 2，3，4-Cl3-C6H2-CH2
95 CH3 CH3 2，3，5-Cl3-C6H2-CH2
96 CH3 CH3 2，3，6-Cl3-C6H2-CH2
97 CH3 CH3 2，4，5-Cl3-C6H2-CH2
98 CH3 CH3 2，4，6-Cl3-C6H2-CH2
99 CH3 CH3 3，4，5-Cl3-C6H2-CH2
100 CH3 CH3 2-Br-C6H4-CH2
101 CH3 CH3 3-Br-C6H4-CH2
102 CH3 CH3 4-Br-C6H4-CH2
103 CH3 CH3 2，3-Br2-C6H3-CH2
104 CH3 CH3 2，4-Br2-C6H3-CH2
105 CH3 CH3 2，5-Br2-C6H3-CH2
106 CH3 CH3 2，6-Br2-C6H3-CH2
107 CH3 CH3 3，4-Br2-C6H3-CH2
108 CH3 CH3 3，5-Br2-C6H3-CH2
109 CH3 CH3 2-F，3-Cl-C6H3-CH2
110 CH3 CH3 2-F，4-Cl-C6H3-CH2
No. R3 R4 R5
111 CH3 CH3 2-F，5-Cl-C6H3-CH2
112 CH3 CH3 2-F，3-Br-C6H3-CH2
113 CH3 CH3 2-F，4-Br-C6H3-CH2
114 CH3 CH3 2-F，5-Br-C6H3-CH2
115 CH3 CH3 2-Cl，3-Br-C6H3-CH2
116 CH3 CH3 2-Cl，4-Br-C6H3-CH2
117 CH3 CH3 2-Cl，5-Br-C6H3-CH2
118 CH3 CH3 3-F，4-Cl-C6H3-CH2
119 CH3 CH3 3-F，5-Cl-C6H3-CH2
120 CH3 CH3 3-F，6-Cl-C6H3-CH2
121 CH3 CH3 3-F，4-Br-C6H3-CH2
122 CH3 CH3 3-F，5-Br-C6H3-CH2
123 CH3 CH3 3-F，6-Br-C6H3-CH2
124 CH3 CH3 3-Cl，4-Br-C6H3-CH2
125 CH3 CH3 3-Cl，5-Br-C6H3-CH2
126 CH3 CH3 3-Cl，6-Br-C6H3-CH2
127 CH3 CH3 4-F，5-Cl-C6H3-CH2
128 CH3 CH3 4-F，6-Cl-C6H3-CH2
129 CH3 CH3 4-F，5-Br-C6H3-CH2
130 CH3 CH3 4-F，6-Br-C6H3-CH2
131 CH3 CH3 4-Cl，5-Br-C6H3-CH2
132 CH3 CH3 5-F，6-Cl-C6H3-CH2
133 CH3 CH3 5-F，6-Br-C6H3-CH2
134 CH3 CH3 5-Cl，6-Br-C6H3-CH2
135 CH3 CH3 3-Br，4-Cl，5-Br-C6H2-CH2
136 CH3 CH3 2-CN-C6H4-CH2
137 CH3 CH3 3-CN-C6H4-CH2
138 CH3 CH3 4-CN-C6H4-CH2
139 CH3 CH3 2-NO2-C6H4-CH2
140 CH3 CH3 3-NO2-C6H4-CH2
141 CH3 CH3 4-NO2-C6H4-CH2
142 CH3 CH3 2-CH3-C6H4-CH2
143 CH3 CH3 3-CH3-C6H4-CH2
144 CH3 CH3 4-CH3-C6H4-CH2
145 CH3 CH3 2，3-(CH3)2-C6H3-CH2
146 CH3 CH3 2，4-(CH3)2-C6H3-CH2
147 CH3 CH3 2，5-(CH3)2-C6H3-CH2
148 CH3 CH3 2，6-(CH3)2-C6H3-CH2
No. R3 R4 R5
149 CH3 CH3 3，4-(CH3)2-C6H3-CH2
150 CH3 CH3 3，5-(CH3)2-C6H3-CH2
151 CH3 CH3 2-C2H5-C6H4-CH2
152 CH3 CH3 3-C2H5-C6H4-CH2
153 CH3 CH3 4-C2H5-C6H4-CH2
154 CH3 CH3 2-i-C3H7-C6H4-CH2
155 CH3 CH3 3-i-C3H7-C6H4-CH2
156 CH3 CH3 4-i-C3H7-C6H4-CH2
157 CH3 CH3 2-cyclohexyl-C6H4-CH2
158 CH3 CH3 3-cyclohexyl-C6H4-CH2
159 CH3 CH3 4-cyclohexyl-C6H4-CH2
160 CH3 CH3 2-vinyl-C6H4-CH2
161 CH3 CH3 3-vinyl-C6H4-CH2
162 CH3 CH3 4-vinyl-C6H4-CH2
163 CH3 CH3 2-allyl-C6H4-CH2
164 CH3 CH3 3-allyl-C6H4-CH2
165 CH3 CH3 4-allyl-C6H4-CH2
166 CH3 CH3 2-C6H5-C6H4-CH2
167 CH3 CH3 3-C6H5-C6H4-CH2
168 CH3 CH3 4-C6H5-C6H4-CH2
169 CH3 CH3 3-CH3，5-t-C4H9-C6H3-CH2
170 CH3 CH3 2-OH-C6H4-CH2
171 CH3 CH3 3-OH-C6H4-CH2
172 CH3 CH3 4-OH-C6H4-CH2
173 CH3 CH3 2-OCH3-C6H4-CH2
174 CH3 CH3 3-OCH3-C6H4-CH2
175 CH3 CH3 4-OCH3-C6H4-CH2
176 CH3 CH3 2，3-(OCH3)2-C6H3-CH2
177 CH3 CH3 2，4-(OCH3)2-C6H3-CH2
178 CH3 CH3 2，5-(OCH3)2-C6H3-CH2
179 CH3 CH3 3，4-(OCH3)2-C6H3-CH2
180 CH3 CH3 3，5-(OCH3)2-C6H3-CH2
181 CH3 CH3 3，4，5-(OCH3)3-C6H2-CH2
182 CH3 CH3 2-OC2H5-C6H4-CH2
183 CH3 CH3 3-OC2H5-C6H4-CH2
184 CH3 CH3 4-OC2H5-C6H4-CH2
185 CH3 CH3 2-O-(n-C3H7)-C6H4-CH2
186 CH3 CH3 3-O-(n-C3H7)-C6H4-CH2
No. R3 R4 R5
187 CH3 CH3 4-O-(n-C3H7)-C6H4-CH2
188 CH3 CH3 2-O-(i-C3H7)-C6H4-CH2
189 CH3 CH3 3-O-(i-C3H7)-C6H4-CH2
190 CH3 CH3 4-O-(i-C3H7)-C6H4-CH2
191 CH3 CH3 4-O-(n-C4H9)-C6H4-CH2
192 CH3 CH3 3-O-(t-C4H9)-C6H4-CH2
193 CH3 CH3 4-O-(n-C6H13)-C6H4-CH2
194 CH3 CH3 2-O-allyl-C6H4-CH2
195 CH3 CH3 3-O-allyl-C6H4-CH2
196 CH3 CH3 4-O-allyl-C6H4-CH2
197 CH3 CH3 2-CF3-C6H4-CH2
198 CH3 CH3 3-CF3-C6H4-CH2
199 CH3 CH3 4-CF3-C6H4-CH2
200 CH3 CH3 2-acetyl-C6H4-CH2
201 CH3 CH3 3-acetyl-C6H4-CH2
202 CH3 CH3 4-acetyl-C6H4-CH2
203 CH3 CH3 2-methoxycarbonyl-C6H4-CH2
204 CH3 CH3 3-methoxycarbonyl-C6H4-CH2
205 CH3 CH3 4-methoxycarbonyl-C6H4-CH2
206 CH3 CH3 2-aminocarbonyl-C6H4-CH2
207 CH3 CH3 3-aminocarbonyl-C6H4-CH2
208 CH3 CH3 4-aminocarbonyl-C6H4-CH2
209 CH3 CH3 2-dimethylaminocarbonyl -C6H4-CH2
210 CH3 CH3 3-dimethylaminocarbonyl -C6H4-CH2
211 CH3 CH3 4-dimethylaminocarbonyl -C6H4-CH2
212 CH3 CH3 2- (N-methylaminocarbonyl) -C6H4-CH2
213 CH3 CH3 3- (N-methylaminocarbonyl) -C6H4-CH2
214 CH3 CH3 4- (N-methylaminocarbonyl) -C6H4-CH2
215 CH3 CH3 2-H2N-C6H4-CH2
216 CH3 CH3 3-H2N-C6H4-CH2
217 CH3 CH3 4-H2N-C6H4-CH2
218 CH3 CH3 2-aminothiocarbonyl-C6H4-CH2
219 CH3 CH3 3-aminothiocarbonyl-C6H4-CH2
220 CH3 CH3 4-aminothiocarbonyl-C6H4-CH2
No. R3 R4 R5
221 CH3 CH3 2-Methoxyiminomethyl-C6H4-CH2
222 CH3 CH3 3-Methoxyiminomethyl-C6H4-CH2
223 CH3 CH3 4-Methoxyiminomethyl-C6H4-CH2
224 CH3 CH3 2-formyl-C6H4-CH2
225 CH3 CH3 3-formyl-C6H4-CH2
226 CH3 CH3 4-formyl-C6H4-CH2
227 CH3 CH3 2- (1' -methoxyimino) Radical-1' -ethyl) -C6H4-CH2
228 CH3 CH3 3- (1' -methoxyimino) Radical-1' -ethyl) -C6H4-CH2
229 CH3 CH3 4- (1' -methoxyimino) Radical-1' -ethyl) -C6H4-CH2
230 CH3 CH3 2-SCH3-C6H4-CH2
231 CH3 CH3 3-SCH3-C6H4-CH2
232 CH3 CH3 4-SCH3-C6H4-CH2
233 CH3 CH3 2-SO2CH3-C6H4-CH2
234 CH3 CH3 3-SO2CH3-C6H4-CH2
235 CH3 CH3 4-SO2CH3-C6H4-CH2
236 CH3 CH3 2-OCF3-C6H4-CH2
237 CH3 CH3 3-OCF3-C6H4-CH2
238 CH3 CH3 4-OCF3-C6H4-CH2
239 CH3 CH3 2-OCHF2-C6H4-CH2
240 CH3 CH3 3-OCHF2-C6H4-CH2
241 CH3 CH3 4-OCHF2-C6H4-CH2
242 CH3 CH3 3-CF3，4-OCF3-C6H3-CH2
243 CH3 CH3 1-naphthyl-CH2
244 CH3 CH3 2-naphthyl-CH2
245 CH3 CH3 2-phenoxyeth-1-yl
246 CH3 CH3 2- (2' -chlorophenoxy) eth-1-yl
247 CH3 CH3 2- (3' -chlorophenoxy) eth-1-yl
248 CH3 CH3 2- (4' -chlorophenoxy) eth-1-yl
249 CH3 CH3 2- (3 ', 5' -Dichlorophenoxy) eth-1-yl
250 CH3 CH3 2- (2' -cyanophenoxy) eth-1-yl
251 CH3 CH3 2- (3' -cyanophenoxy) eth-1-yl
252 CH3 CH3 2- (4' -cyanophenoxy) eth-1-yl
253 CH3 CH3 2- (2' -methylphenoxy) eth-1-yl
254 CH3 CH3 2- (3' -methylphenoxy) eth-1-yl
255 CH3 CH3 2- (4' -methylphenoxy) eth-1-yl
No. R3 R4 R5
256 CH3 CH3 2- (3' -tert-butylphenoxy) 1-ethyl radical
257 CH3 CH3 2- (4' -tert-butylphenoxy) 1-ethyl radical
258 CH3 CH3 2- (2' -Nitrophenoxy) eth-1-yl
259 CH3 CH3 2- (3' -Nitrophenoxy) eth-1-yl
260 CH3 CH3 2- (4' -Nitrophenoxy) eth-1-yl
261 CH3 CH3 2- (2' -methoxyphenoxy) 1-ethyl radical
262 CH3 CH3 2- (3' -methoxyphenoxy) 1-ethyl radical
263 CH3 CH3 2- (4' -methoxyphenoxy) 1-ethyl radical
264 CH3 CH3 2- (2' -trifluoromethylphenoxy) 1-ethyl radical
265 CH3 CH3 2- (3' -trifluoromethylphenoxy) 1-ethyl radical
266 CH3 CH3 2- (4' -trifluoromethylphenoxy) 1-ethyl radical
267 CH3 CH3 2- (2' -Acetylphenoxy) eth-1-yl
268 CH3 CH3 2- (3' -Acetylphenoxy) eth-1-yl
269 CH3 CH3 2- (4' -Acetylphenoxy) eth-1-yl
270 CH3 CH3 2- (2' -methoxycarbonyl) 1-ethyl radical
271 CH3 CH3 2- (3' -methoxycarbonyl) 1-ethyl radical
272 CH3 CH3 2- (4' -methoxycarbonyl) 1-ethyl radical
273 CH3 CH3 2- (2' -dimethylaminocarbonyl) 1-ethyl radical
274 CH3 CH3 2- (3' -dimethylaminocarbonyl) 1-ethyl radical
275 CH3 CH3 2- (4' -dimethylaminocarbonyl) 1-ethyl radical
276 CH3 CH3 2- (2' -aminothiocarbonyl) 1-ethyl radical
277 CH3 CH3 2- (3' -aminothiocarbonyl) 1-ethyl radical
278 CH3 CH3 2- (4' -aminothiocarbonyl) 1-ethyl radical
279 CH3 CH3 2- (2' -methylsulfonyl) 1-ethyl radical
280 CH3 CH3 2- (3' -methylsulfonyl) 1-ethyl radical
No. R3 R4 R5
281 CH3 CH3 2- (4' -methylsulfonyl) 1-ethyl radical
282 CH3 CH3 3-Phenoxyprop-1-yl
283 CH3 CH3 3- (2' -chlorophenoxy) Prop-1-yl
284 CH3 CH3 3- (3' -chlorophenoxy) Prop-1-yl
285 CH3 CH3 3- (4' -chlorophenoxy) Prop-1-yl
286 CH3 CH3 3- (3 ', 5', dichlorophenoxy) Prop-1-yl
287 CH3 CH3 3- (2' -Cyanophenoxy) propan-1-yl
288 CH3 CH3 3- (3' -Cyanophenoxy) propan-1-yl
289 CH3 CH3 3- (4' -Cyanophenoxy) propan-1-yl
290 CH3 CH3 3- (2' -methylphenoxy) Prop-1-yl
291 CH3 CH3 3- (3' -methylphenoxy) Prop-1-yl
292 CH3 CH3 3- (4' -methylphenoxy) Prop-1-yl
293 CH3 CH3 3- (2' -methoxy)Radical phenoxy) Prop-1-yl
294 CH3 CH3 3- (3' -methoxyphenoxy) Prop-1-yl
295 CH3 CH3 3- (4' -methoxyphenoxy) Prop-1-yl
296 CH3 CH3 3- (2' -trifluoromethylphenoxy) Prop-1-yl
297 CH3 CH3 3- (3' -trifluoromethylbenzene)Oxy radical) Prop-1-yl
298 CH3 CH3 3- (4' -trifluoromethylphenoxy) Prop-1-yl
299 CH3 CH3 4-phenoxybut-1-yl
300 CH3 CH3 2-Phenylethan-1-yl
301 CH3 CH3 2- (2' -chlorophenyl) eth-1-yl
302 CH3 CH3 2- (3' -chlorophenyl) eth-1-yl
303 CH3 CH3 2- (4' -chlorophenyl) eth-1-yl
304 CH3 CH3 2- (3 ', 5' -dichlorophenyl) eth-1-yl
305 CH3 CH3 2- (2' -cyanophenyl) eth-1-yl
306 CH3 CH3 2- (3' -cyanophenyl) eth-1-yl
307 CH3 CH3 2- (4' -cyanophenyl) eth-1-yl
308 CH3 CH3 2- (2' -methylphenyl) ethan-1-yl
No. R3 R4 R5
309 CH3 CH3 2- (3' -methylphenyl) ethan-1-yl
310 CH3 CH3 2- (4' -methylphenyl) eth-1-yl
311 CH3 CH3 2- (2' -methoxyphenyl) eth-1-yl
312 CH3 CH3 2- (3' -methoxyphenyl) eth-1-yl
313 CH3 CH3 2- (4' -methoxyphenyl) eth-1-yl
314 CH3 CH3 2- (2' -trifluoromethylphenyl) 1-ethyl radical
315 CH3 CH3 2- (3' -trifluoromethylphenyl) 1-ethyl radical
316 CH3 CH3 2- (4' -trifluoromethylphenyl) 1-ethyl radical
317 CH3 CH3 3-phenylpropan-1-yl
318 CH3 CH3 3- (2' -chlorophenyl) propan-1-yl
319 CH3 CH3 3- (3' -chlorophenyl) propan-1-yl
320 CH3 CH3 3- (4' -chlorophenyl) propan-1-yl
321 CH3 CH3 3- (2' -cyanophenyl) propan-1-yl
322 CH3 CH3 3- (3' -cyanophenyl) propan-1-yl
323 CH3 CH3 3- (4' -cyanophenyl) propan-1-yl
324 CH3 CH3 3- (2' -trifluoromethylphenyl) Prop-1-yl
325 CH3 CH3 4-Phenylbut-1-yl
326 CH3 CH3 4- (4' -chlorophenyl) but-1-yl
327 CH3 CH3 6- (4' -chlorophenyl) hex-1-yl
328 CH3 CH3 2-pyridylmethyl
329 CH3 CH3 3-pyridylmethyl
330 CH3 CH3 4-pyridylmethyl
331 CH3 CH3 4-Chloropyridin-2-ylmethyl
332 CH3 CH3 5-Chloropyridin-2-ylMethyl radical
333 CH3 CH3 6-Chloropyridin-2-ylmethyl
334 CH3 CH3 5-Chloropyridin-3-ylmethyl
335 CH3 CH3 6-Chloropyridin-3-ylmethyl
336 CH3 CH3 2-Chloropyridin-4-ylmethyl
337 CH3 CH3 2-pyrimidinylmethyl
338 CH3 CH3 4-Chloropyrimidin-2-ylmethyl
339 CH3 CH3 5-Chloropyrimidin-2-ylmethyl
340 CH3 CH3 2-Chloropyrimidin-4-ylmethyl
341 CH3 CH3 6-Chloropyrimidin-4-ylmethyl
342 CH3 CH3 2-Chloropyrimidin-5-ylmethyl
343 CH3 CH3 4-pyridazinylmethyl
344 CH3 CH3 2-pyrazinylmethyl
No. R3 R4 R5
345 CH3 CH3 5-Chloropyrazin-2-ylmethyl
346 CH3 CH3 6-Chloropyrazin-2-ylmethyl
347 CH3 CH3 3-pyridazinylmethyl
348 CH3 CH3 6-Chloropyridazin-3-ylmethyl
349 CH3 CH3 1, 3, 5-triazinylmethyl
350 CH3 CH3 2-furyl methyl group
351 CH3 CH3 3-furyl methyl group
352 CH3 CH3 4-Bromofuran-2-ylmethyl
353 CH3 CH3 5-Chlorofuran-2-ylmethyl
354 CH3 CH3 2-thienylmethyl
355 CH3 CH3 3-thienylmethyl
356 CH3 CH3 5-methylthiophen-3-ylmethyl
357 CH3 CH3 5-chlorothien-2-ylmethyl
358 CH3 CH3 2-chlorothiophen-4-ylmethyl
359 CH3 CH3 2-pyrrolylmethyl
360 CH3 CH3 3-pyrrolylmethyl
361 CH3 CH3 2-oxazolylmethyl
362 CH3 CH3 4-Methyloxazol-2-ylmethyl
363 CH3 CH3 5-Methyloxazol-2-ylmethyl
364 CH3 CH3 4-Chlorooxazol-2-ylmethyl
365 CH3 CH3 5-Chlorooxazol-2-ylmethyl
366 CH3 CH3 4-oxazolylmethyl
367 CH3 CH3 2-methyloxazol-4-ylmethyl
368 CH3 CH3 5-Methyloxazol-4-ylmethyl
369 CH3 CH3 2-Chlorooxazol-4-ylmethyl
370 CH3 CH3 5-Chlorooxazol-4-ylmethyl
371 CH3 CH3 5-oxazolylmethyl
372 CH3 CH3 2-methyloxazol-5-ylmethyl
373 CH3 CH3 4-Methyloxazol-5-ylmethyl
374 CH3 CH3 2-Chlorooxazol-5-ylmethyl
375 CH3 CH3 4-Chlorooxazol-5-ylmethyl
376 CH3 CH3 2-Thiazolylmethyl
377 CH3 CH3 4-Methylthiazol-2-ylmethyl
378 CH3 CH3 5-Methylthiazol-2-ylmethyl
379 CH3 CH3 4-Chlorothiazol-2-ylmethyl
380 CH3 CH3 5-Chlorothiazol-2-ylmethyl
381 CH3 CH3 4-Thiazolylmethyl
382 CH3 CH3 2-Methylthiazol-4-ylmethyl
No. R3 R4 R5
383 CH3 CH3 5-Methylthiazol-4-ylmethyl
384 CH3 CH3 2-Chlorothiazol-4-ylmethyl
385 CH3 CH3 5-Chlorothiazol-4-ylmethyl
386 CH3 CH3 5-Thiazolylmethyl
387 CH3 CH3 2-Methylthiazol-5-ylmethyl
388 CH3 CH3 4-Methylthiazol-5-ylmethyl
389 CH3 CH3 2-Chlorothiazol-5-ylmethyl
390 CH3 CH3 4-Chlorothiazol-5-ylmethyl
391 CH3 CH3 3-isoxazolylmethyl
392 CH3 CH3 4-methylisoxazol-3-ylmethyl
393 CH3 CH3 5-methylisoxazol-3-ylmethyl
394 CH3 CH3 4-Chloroisisoxazol-3-ylmethyl
395 CH3 CH3 5-Chloroisisoxazol-3-ylmethyl
396 CH3 CH3 4-isoxazolylmethyl
397 CH3 CH3 3-methylisoxazol-4-ylmethyl
398 CH3 CH3 5-methylisoxazol-4-ylmethyl
399 CH3 CH3 3-chloro-isoxazol-4-ylmethyl
400 CH3 CH3 5-Chloroisisoxazol-4-ylmethyl
401 CH3 CH3 5-isoxazolylmethyl
402 CH3 CH3 3-methylisoxazol-5-ylmethyl
403 CH3 CH3 4-methylisoxazol-5-ylmethyl
404 CH3 CH3 3-chloro-isoxazol-5-ylmethyl
405 CH3 CH3 4-Chloroisisoxazol-5-ylmethyl
406 CH3 CH3 3-isothiazolylmethyl
407 CH3 CH3 4-methylisothiazole-3- Radical methyl
408 CH3 CH3 5-methylisothiazole-3- Radical methyl
409 CH3 CH3 4-chloro-isothiazole-3- Radical methyl
410 CH3 CH3 5-chloro-isothiazole-3- Radical methyl
411 CH3 CH3 4-isothiazolylmethyl
412 CH3 CH3 3-methylisothiazole-4- Radical methyl
413 CH3 CH3 5-methylisothiazole-4- Radical methyl
414 CH3 CH3 3-chloro-isothiazole-4- Radical methyl
415 CH3 CH3 5-chloro-isothiazole-4- Radical methyl
No. R3 R4 R5
416 CH3 CH3 5-Isothiazolylmethyl
417 CH3 CH3 3-methylisothiazole-5- Radical methyl
418 CH3 CH3 4-methylisothiazole-5- Radical methyl
419 CH3 CH3 3-chloro-isothiazole-5- Radical methyl
420 CH3 CH3 4-chloro-isothiazole-5- Radical methyl
421 CH3 CH3 4-imidazolylmethyl
422 CH3 CH3 1-phenylpyrazol-3-ylmethyl
423 CH3 CH3 1-methylimidazol-4-ylmethyl
424 CH3 CH3 1-phenyl-1, 2, 4-triazole-3- Radical methyl
425 CH3 CH3 1, 2, 4-oxadiazol-3-ylmethyl
426 CH3 CH3 5-chloro-1, 2, 4-oxadiazole-3- Radical methyl
427 CH3 CH3 5-methyl-1, 2, 4-oxadiazole-3- Radical methyl
428 CH3 CH3 5-trifluoromethyl-1, 2, 4-oxadiazole-3- Radical methyl
429 CH3 CH3 1, 3, 4-oxadiazol-2-ylmethyl
430 CH3 CH3 5-chloro-1, 3, 4-oxadiazole-2- Radical methyl
431 CH3 CH3 5-methyl-1, 3, 4-oxadiazole-2- Radical methyl
432 CH3 CH3 5-methoxy-1, 3, 4-oxadiazole-2- Radical methyl
433 CH3 CH3 1, 2, 4-Thiadiazol-3-ylmethyl
434 CH3 CH3 5-chloro-1, 2, 4-thiadiazole-3- Radical methyl
435 CH3 CH3 5-methyl-1, 2, 4-thiadiazole-3- Radical methyl
436 CH3 CH3 1, 3, 4-Thiadiazol-2-ylmethyl
437 CH3 CH3 5-chloro-1, 3, 4-thiadiazole-2- Radical methyl
438 CH3 CH3 5-methyl-1, 3, 4-thiadiazole-2- Radical methyl
439 CH3 CH3 5-cyano-1, 3, 4-thiadiazole-2- Radical methyl
440 CH3 CH3 2- (2' -pyridyloxy) eth-1-yl
441 CH3 CH3 2- (3' -pyridyloxy) eth-1-yl
442 CH3 CH3 2- (4' -pyridyloxy) eth-1-yl
No. R3 R4 R5
443 CH3 CH3 2- (2' -pyrimidinyloxy) 1-ethyl radical
444 CH3 CH3 2- (4' -pyrimidinyloxy) 1-ethyl radical
445 CH3 CH3 2- (5' -pyrimidinyloxy) - 1-ethyl radical
446 CH3 CH3 2- (2' -pyridazinyloxy) eth-1-yl
447 CH3 CH3 2- (2' -pyridazinyloxy) 1-ethyl radical
448 CH3 CH3 2- (3' -pyridazinyloxy) 1-ethyl radical
449 CH3 CH3 2- (1 ', 3 ', 5 ' -triazinyloxy) 1-ethyl radical
450 CH3 CH3 2- (5 '-methylisoxazol-3' -yl-oxy) 1-ethyl radical
451 CH3 CH3 2- (5 '-chloroisoxazol-3' -yl-oxy) 1-ethyl radical
452 CH3 CH3 2- (2 '-methoxythiazol-4' -yl-oxy) 1-ethyl radical
453 CH3 CH3 2- (4 '-chlorooxazol-2' -yl-oxy) 1-ethyl radical
454 CH3 CH3 2- (1 ' -phenyl-1 ' H-1 ', 2 ', 4 ' -triazine -3' -yloxy) eth-1-yl
455 CH3 CH3 2- (1 '-phenylpyrazolyl-3' -yl-oxy) 1-ethyl radical
456 CH3 CH3 C6H5
457 CH3 CH3 2-Cl-C6H4
458 CH3 CH3 3-Cl-C6H4
459 CH3 CH3 4-Cl-C6H4
460 CH3 CH3 2，3-Cl2-C6H3
461 CH3 CH3 2，4-Cl2-C6H3
462 CH3 CH3 2，5-Cl2-C6H3
463 CH3 CH3 3，4-Cl2-C6H3
464 CH3 CH3 3，5-Cl2-C6H3
465 CH3 CH3 4-CN-C6H4
466 CH3 CH3 2-NO2-C6H4
467 CH3 CH3 3-NO2-C6H4
468 CH3 CH3 4-NO2-C6H4
469 CH3 CH3 2，4-(NO2)2-C6H3
470 CH3 CH3 2-CH3-C6H4
471 CH3 CH3 3-CH3-C6H4
472 CH3 CH3 4-CH3-C6H4
No. R3 R4 R5
473 CH3 CH3 2，3-(CH3)2-C6H3
474 CH3 CH3 2，4-(CH3)2-C6H3
475 CH3 CH3 2，5-(CH3)2-C6H3
476 CH3 CH3 2，6-(CH3)2-C6H3
477 CH3 CH3 2-C6H5-C6H4
478 CH3 CH3 3-C6H5-C6H4
479 CH3 CH3 4-C6H5-C6H4
480 CH3 CH3 3-OCH3-C6H4
481 CH3 CH3 4-OCH3-C6H4
482 CH3 CH3 3-acetyl-C6H4
483 CH3 CH3 4-acetyl-C6H4
484 CH3 CH3 3-methoxycarbonyl-C6H4
485 CH3 CH3 4-methoxycarbonyl-C6H4
486 CH3 CH3 3-CF3-C6H4
487 CH3 CH3 4-CF3-C6H4
488 CH3 CH3 2-naphthyl radical
489 CH3 CH3 6-Chloropyridazin-3-yl
490 CH3 CH3 5-chloropyrazin-2-yl
491 CH3 CH3 Quinolin-2-yl
492 CH3 CH3 2, 5-dimethylpyrazin-3-yl
493 CH3 CH3 Pyrazin-2-yl radicals
494 CH3 CH3 3-chloropyridin-2-yl
495 CH3 CH3 6-chloropyridin-2-yl
496 CH3 CH3 4-trifluoromethyl, 6-chloropyridine -2-yl
497 CH3 CH3 4-Trifluoromethylpyridin-2-yl
498 CH3 CH3 6-Trifluoromethylpyridin-2-yl
499 CH3 CH3 6-methoxypyridin-2-yl
500 CH3 CH3 5-Chloropyridin-2-yl
501 CH3 CH3 Pyridin-2-yl
502 CH3 CH3 Benzothiazol-2-yl
503 CH3 CH3 7-chloroquinolin-4-yl
504 CH3 CH3 3-Nitropyridin-2-yl
505 CH3 CH3 Pyrrol-3-yl
506 CH3 CH3 Pyrrol-2-yl
507 CH3 CH3 2, 6-dinitropyridin-4-yl
508 CH3 CH3 5-Nitro radicalPyridin-2-yl
509 CH3 CH3 Pyridin-4-yl
510 CH3 CH3 Pyridin-3-yl
No. R3 R4 R5
511 CH3 CH3 Pyrimidin-2-yl
512 CH3 CH3 Pyrimidin-4-yl
513 CH3 CH3 Quinazolin-4-yl
514 CH3 CH3 6-Chloropyrimidin-4-yl
515 CH3 CH3 6-methoxypyrimidin-4-yl
516 CH3 CH3 2, 5, 6-IIIChloropyrimidin-4-yl radical 4-yl
517 CH3 CH3 2, 6-dimethylpyrimidin-4-yl
518 CH3 CH3 A 2-methyl group, 6-Chloropyrimidin-4-yl
519 CH3 CH3 2-methyl, 6-ethoxypyrimidine -4-yl
520 CH3 CH3 4, 5, 6-trichloropyrimidines -2-yl
521 CH3 CH3 4, 6-Dimethoxypyrimidin-2-yl
522 CH3 CH3 4, 6-dimethylpyrimidin-2-yl
523 CH3 CH3 4, 6-dichloropyrimidin-2-yl
524 CH3 CH3 4-methyl, 6-methoxypyrimidine -2-yl
525 CH3 CH3 4-chloro, 6-methoxypyrimidine -2-yl
526 CH3 CH3 6-chloroquinoxalin-2-yl
527 CH3 CH3 3, 6-dichloro-1, 2, 4-triazine -5-yl
528 CH3 CH3 4-methoxy-1, 3, 5-triazin-2-yl
529 CH3 CH3 4-ethoxy-1, 3, 5-triazin-2-yl
530 CH3 CH3 4, 6-dichloro-1, 3, 5-triazine -2-yl
531 CH3 CH3 4-ethoxy, 6-chloro- 1, 3, 5-triazin-2-yl
532 CH3 CH3 Isoxazol-3-yl
533 CH3 CH3 Thien-2-yl
534 CH3 CH3 Furan-2-yl
535 CH3 CH3 Thiatriazol-5-yl
536 CH3 CH3 (E) -1-chloropropen-3-yl
537 CH3 CH3 (E) -4- (4' -chlorophenyl) but-2-ene -1-yl
538 CH3 CH3 Propin-3-yl
539 CH3 CH3 Methyl carbonyl
540 CH3 CH3 Ethyl carbonyl
541 CH3 CH3 n-propylcarbonyl
542 CH3 CH3 i-propylcarbonyl group
No. R3 R4 R5
543 CH3 CH3 n-butylcarbonyl group
544 CH3 CH3 s-butylcarbonyl group
545 CH3 CH3 i-butylcarbonyl group
546 CH3 CH3 t-butylcarbonyl group
547 CH3 CH3 n-pentylcarbonyl group
548 CH3 CH3 i-pentylcarbonyl group
549 CH3 CH3 Neo-pentylcarbonyl
550 CH3 CH3 n-hexylcarbonyl group
551 CH3 CH3 n-octyl carbonyl
552 CH3 CH3 1-propenyl carbonyl
553 CH3 CH3 2-penten-1-ylcarbonyl
554 CH3 CH3 2, 5-heptadiene-1- Radical carbonyl
555 CH3 CH3 Benzoyl radical
556 CH3 CH3 2-chlorobenzoyl
557 CH3 CH3 3-chlorobenzoyl
558 CH3 CH3 4-chlorobenzoyl
559 CH3 CH3 2-cyanobenzoyl
560 CH3 CH3 3-cyanobenzoyl
561 CH3 CH3 4-cyanobenzoyl
562 CH3 CH3 4-methoxybenzoyl
563 CH3 CH3 2-pyridylcarbonyl
564 CH3 CH3 3-pyridylcarbonyl
565 CH3 CH3 4-pyridylcarbonyl
566 CH3 CH3 2-pyrimidylcarbonyl
567 CH3 CH3 2-oxazolylcarbonyl
568 CH3 CH3 4-methylisoxazole-5- Radical carbonyl
569 CH3 CH3 Mesyl radical
570 CH3 CH3 Ethanesulfonyl radical
571 CH3 CH3 n-propanesulfonyl radical
572 CH3 CH3 i-propanesulfonyl radical
573 CH3 CH3 n-butanesulfonyl group
574 CH3 CH3 t-butylsulfonyl group
575 CH3 CH3 n-pentanesulfonyl
576 CH3 CH3 Novel pentanesulfonyl radicals
577 CH3 CH3 n-hexanesulfonyl
578 CH3 CH3 n-octanesulfonyl radical
579 CH3 CH3 Benzenesulfonyl radical
No. R3 R4 R5
580 CH3 CH3 2-Chlorobenzenesulfonyl
581 CH3 CH3 3-Chlorophenesulfonyl
582 CH3 CH3 4-Chlorobenzenesulfonyl
583 CH3 CH3 2-cyanophenylsulphonyl
584 CH3 CH3 3-cyanophenylsulfonyl group
585 CH3 CH3 4-cyanophenylsulphonyl
586 CH3 CH3 2-pyridylsulfonyl
587 CH3 CH3 3-pyridylsulfonyl
588 CH3 CH3 4-pyridylsulfonyl
589 CH3 CH3 2-pyrimidinylsulfonyl radical
590 CH3 CH3 4-oxazolylsulfonyl
591 CH3 CH3 5-chlorothiazole-2- Radical sulfonyl radical
592 CH3 CH3 2-t-C4H9-C6H4-CH2
593 CH3 CH3 3-t-C4H9-C6H4-CH2
594 CH3 CH3 4-t-C4H9-C6H4-CH2
595 CH3 CH3 2- (4 '-chlorothiazol-2' -yloxy) 1-ethyl radical
596 CH3 CH3 2- (1 '-methylpyrrole-4' -yloxy) 1-ethyl radical
597 CH3 CH3 4-Br-C6H4
598 CH3 CH3 3，5-(CH3)2-C6H3
599 CH3 CH3 4-C2H5-C6H4
600 CH3 CH3 3-dimethylaminocarbonyl-C6H4
601 CH3 CH3 4-dimethylaminocarbonyl-C6H4
602 CH3 CH3 2-hydroxypropan-1-yl
603 CH3 CH3 6-hydroxy-2-methylpyrimidine -4-ylmethyl
604 CH3 CH3 [6-OH，2-CH(CH3)2-pyrimidine-4- Base of]-CH2
605 CH3 CH3 [6-OH，2-CH(CH2)2-pyrimidine-4- Base of]-CH2
606 CH3 CH3 5- (2' -Furan) -pent-1-yl
607 CH3 CH3 5- (2' -N-methylpyrrole) -pent-1-yl
608 CH3 CH3 [2-(4-Cl-C6H4) -oxazol-4-yl]- CH2
609 CH3 CH3 3-CF3-pyridin-2-yl
610 CH3 CH3 5-CF3-pyridin-2-yl
611 CH3 CH3 6- (2' -thienyl) hex-1-yl
612 CH3 t-C4H9 H
No. R3 R4 R5
613 CH3 t-C4H9 CH3
614 CH3 t-C4H9 C2H5
615 CH3 t-C4H9 n-C3H7
616 CH3 t-C4H9 i-C3H7
617 CH3 t-C4H9 Cyclopropyl group
618 CH3 t-C4H9 n-C4H9
619 CH3 t-C4H9 t-C4H9
620 CH3 t-C4H9 n-C6H13
621 CH3 t-C4H9 (E) -1-chloropropen-3-yl
622 CH3 t-C4H9 Propin-3-yl
623 CH3 t-C4H9 3-methylbut-2-en-1-yl
624 CH3 t-C4H9 2-naphthyl-CH2
625 CH3 t-C4H9 4-Cl-C6H4-CH2
626 CH3 t-C4H9 (E) -4- (4' -chlorophenyl) but-2-ene -1-yl
627 CH3 t-C4H9 6- (4' -chlorophenyl) hex-1-yl
628 CH3 t-C4H9 3-CF3-C6H4
629 CH3 C6H5 H
630 CH3 C6H5 CH3
631 CH3 C6H5 C2H5
632 CH3 C6H5 n-C3H7
633 CH3 C6H5 i-C3H7
634 CH3 C6H5 Cyclopropyl group
635 CH3 C6H5 n-C4H9
636 CH3 C6H5 t-C4H9
637 CH3 C6H5 n-C6H13
638 CH3 C6H5 4-Cl-C6H4-CH2
639 CH3 C6H5 3-CF3-C6H4
640 CH3 C6H5 6- (4' -chlorophenyl) hex-1-yl
641 CH3 C6H5 (E) -4- (4' -chlorophenyl) but-2-ene -1-yl
642 CH3 H H
643 CH3 H CH3
644 CH3 H C2H5
645 CH3 H n-C3H7
646 CH3 H i-C3H7
647 CH3 OH H
648 CH3 OH CH3
649 CH3 OH C2H5
No. R3 R4 R5
650 CH3 OH n-C3H7
651 CH3 OH i-C3H7
652 CH3 Cl CH3
653 CH3 Cl C2H5
654 CH3 Cl n-C3H7
655 CH3 Cl i-C3H7
656 CH3 OCH3 H
657 CH3 OCH3 CH3
658 CH3 OCH3 C2H5
659 CH3 OCH3 n-C3H7
660 CH3 OCH3 i-C3H7
661 CH3 SCH3 H
662 CH3 SCH3 CH3
663 CH3 SCH3 C2H5
664 CH3 SCH3 n-C3H7
665 CH3 SCH3 i-C3H7
666 CH3 Cyclopropyl group H
667 CH3 Cyclopropyl group CH3
668 CH3 Cyclopropyl group C2H5
669 CH3 Cyclopropyl group n-C3H7
670 CH3 Cyclopropyl group i-C3H7
671 CH3 2-pyridyl group H
672 CH3 2-pyridyl group CH3
673 CH3 2-pyridyl group C2H5
674 CH3 2-pyridyl group n-C3H7
675 CH3 2-pyridyl group i-C3H7
676 CH3 3-pyridyl group H
677 CH3 3-pyridyl group CH3
678 CH3 3-pyridyl group C2H5
679 CH3 3-pyridyl group n-C3H7
680 CH3 3-pyridyl group i-C3H7
681 CH3 4-pyridyl group H
682 CH3 4-pyridyl group CH3
683 CH3 4-pyridyl group C2H5
684 CH3 4-pyridyl group n-C3H7
685 CH3 4-pyridyl group i-C3H7
686 CH3 2-pyrimidinyl radicals H
687 CH3 2-pyrimidinyl radicals CH3
No. R3 R4 R5
688 CH3 2-pyrimidinyl radicals C2H5
689 CH3 2-pyrimidinyl radicals n-C3H7
690 CH3 2-pyrimidinyl radicals i-C3H7
691 CH3 4-pyrimidinyl radicals H
692 CH3 4-pyrimidinyl radicals CH3
693 CH3 4-pyrimidinyl radicals C2H5
694 CH3 4-pyrimidinyl radicals n-C3H7
695 CH3 4-pyrimidinyl radicals i-C3H7
696 CH3 5-pyrimidinyl radicals H
697 CH3 5-pyrimidinyl radicals CH3
698 CH3 5-pyrimidinyl radicals C2H5
699 CH3 5-pyrimidinyl radicals n-C3H7
700 CH3 5-pyrimidinyl radicals i-C3H7
701 CH3 1, 3, 5-triazinyl H
702 CH3 1, 3, 5-triazinyl CH3
703 CH3 1, 3, 5-triazinyl C2H5
704 CH3 1, 3, 5-triazinyl n-C3H7
705 CH3 1, 3, 5-triazinyl i-C3H7
706 CH3 2-furyl radical H
707 CH3 2-furyl radical CH3
708 CH3 2-furyl radical C2H5
709 CH3 2-furyl radical n-C3H7
710 CH3 2-furyl radical i-C3H7
711 CH3 3-furyl radical H
712 CH3 3-furyl radical CH3
713 CH3 3-furyl radical C2H5
714 CH3 3-furyl radical n-C3H7
715 CH3 3-furyl radical i-C3H7
716 CH3 2-thienyl radical H
717 CH3 2-thienyl radical CH3
718 CH3 2-thienyl radical C2H5
719 CH3 2-thienyl radical n-C3H7
720 CH3 2-thienyl radical i-C3H7
721 CH3 3-thienyl radical H
722 CH3 3-thienyl radical CH3
723 CH3 3-thienyl radical C2H5
724 CH3 3-thienyl radical n-C3H7
725 CH3 3-thienyl radical i-C3H7
No. R3 R4 R5
726 CH3 2-oxazolyl radical H
727 CH3 2-oxazolyl radical CH3
728 CH3 2-oxazolyl radical C2H5
729 CH3 2-oxazolyl radical n-C3H7
730 CH3 2-oxazolyl radical i-C3H7
731 CH3 4-oxazolyl radical H
732 CH3 4-oxazolyl radical CH3
733 CH3 4-oxazolyl radical C2H5
734 CH3 4-oxazolyl radical n-C3H7
735 CH3 4-oxazolyl radical i-C3H7
736 CH3 2-thiazolyl group H
737 CH3 2-thiazolyl group CH3
738 CH3 2-thiazolyl group C2H5
739 CH3 2-thiazolyl group n-C3H7
740 CH3 2-thiazolyl group i-C3H7
741 CH3 4-thiazolyl group H
742 CH3 4-thiazolyl group CH3
743 CH3 4-thiazolyl group C2H5
744 CH3 4-thiazolyl group n-C3H7
745 CH3 4-thiazolyl group i-C3H7
746 CH3 3-isoxazolyl H
747 CH3 3-isoxazolyl CH3
748 CH3 3-isoxazolyl C2H5
749 CH3 3-isoxazolyl n-C3H7
750 CH3 3-isoxazolyl i-C3H7
751 CH3 5-isoxazolyl H
752 CH3 5-isoxazolyl CH3
753 CH3 5-isoxazolyl C2H5
754 CH3 5-isoxazolyl n-C3H7
755 CH3 5-isoxazolyl i-C3H7
756 CH3 2-imidazolyl H
757 CH3 2-imidazolyl CH3
758 CH3 2-imidazolyl C2H5
759 CH3 2-imidazolyl n-C3H7
760 CH3 2-imidazolyl i-C3H7
761 CH3 3-pyrazolyl radical H
762 CH3 3-pyrazolyl radical CH3
763 CH3 3-pyrazolyl radical C2H5
No. R3 R4 R5
764 CH3 3-pyrazolyl radical n-C3H7
765 CH3 3-pyrazolyl radical i-C3H7
766 CH3 4-pyrazolyl radical H
767 CH3 4-pyrazolyl radical CH3
768 CH3 4-pyrazolyl radical C2H5
769 CH3 4-pyrazolyl radical n-C3H7
770 CH3 4-pyrazolyl radical i-C3H7
771 OCH3 H H
772 OCH3 H CH3
773 OCH3 H C2H5
774 OCH3 H n-C3H7
775 OCH3 H i-C3H7
776 OCH3 OH H
777 OCH3 OH CH3
778 OCH3 OH C2H5
779 OCH3 OH n-C3H7
780 OCH3 OH i-C3H7
781 OCH3 Cl n-C4H9
782 OCH3 Cl CH3
783 OCH3 Cl C2H5
784 OCH3 Cl n-C3H7
785 OCH3 Cl i-C3H7
786 OCH3 OCH3 H
787 OCH3 OCH3 CH3
788 OCH3 OCH3 C2H5
789 OCH3 OCH3 n-C3H7
790 OCH3 OCH3 i-C3H7
791 OCH3 SCH3 H
792 OCH3 SCH3 CH3
793 OCH3 SCH3 C2H5
794 OCH3 SCH3 n-C3H7
795 OCH3 SCH3 i-C3H7
796 OCH3 CH3 H
797 OCH3 CH3 CH3
798 OCH3 CH3 C2H5
799 OCH3 CH3 n-C3H7
800 OCH3 CH3 i-C3H7
801 OCH3 Cyclopropyl group H
No. R3 R4 R5
802 OCH3 Cyclopropyl group CH3
803 OCH3 Cyclopropyl group C2H5
804 OCH3 Cyclopropyl group n-C3H7
805 OCH3 Cyclopropyl group i-C3H7
806 OCH3 2-pyridyl group H
807 OCH3 2-pyridyl group CH3
808 OCH3 2-pyridyl group C2H5
809 OCH3 2-pyridyl group n-C3H7
810 OCH3 2-pyridyl group i-C3H7
811 OCH3 3-pyridyl group H
812 OCH3 3-pyridyl group CH3
813 OCH3 3-pyridyl group C2H5
814 OCH3 3-pyridyl group n-C3H7
815 OCH3 3-pyridyl group i-C3H7
816 OCH3 4-pyridyl group H
817 OCH3 4-pyridyl group CH3
818 OCH3 4-pyridyl group C2H5
819 OCH3 4-pyridyl group n-C3H7
820 OCH3 4-pyrimidinyl radicals i-C3H7
821 OCH3 2-pyrimidinyl radicals H
822 OCH3 2-pyrimidinyl radicals CH3
823 OCH3 2-pyrimidinyl radicals C2H5
824 OCH3 2-pyrimidinyl radicals n-C3H7
825 OCH3 2-pyrimidinyl radicals i-C3H7
826 OCH3 4-pyrimidinyl radicals H
827 OCH3 4-pyrimidinyl radicals CH3
828 OCH3 4-pyrimidinyl radicals C2H5
829 OCH3 4-pyrimidinyl radicals n-C3H7
830 OCH3 4-pyrimidinyl radicals i-C3H7
831 OCH3 5-pyrimidinyl radicals H
832 OCH3 5-pyrimidinyl radicals CH3
833 OCH3 5-pyrimidinyl radicals C2H5
834 OCH3 5-pyrimidinyl radicals n-C3H7
835 OCH3 5-pyrimidinyl radicals i-C3H7
836 OCH3 1, 3, 5-triazinyl H
837 OCH3 1, 3, 5-triazinyl CH3
838 OCH3 1, 3, 5-triazinyl C2H5
839 OCH3 1, 3, 5-triazinyl n-C3H7
No. R3 R4 R5
840 OCH3 1, 3, 5-triazinyl i-C3H7
841 OCH3 2-furyl radical H
842 OCH3 2-furyl radical CH3
843 OCH3 2-furyl radical C2H5
844 OCH3 2-furyl radical n-C3H7
845 OCH3 2-furyl radical i-C3H7
846 OCH3 3-furyl radical H
847 OCH3 3-furyl radical CH3
848 OCH3 3-furyl radical C2H5
849 OCH3 3-furyl radical n-C3H7
850 OCH3 3-furyl radical i-C3H7
851 OCH3 2-thienyl radical H
852 OCH3 2-thienyl radical CH3
853 OCH3 2-thienyl radical C2H5
854 OCH3 2-thienyl radical n-C3H7
855 OCH3 2-thienyl radical i-C3H7
856 OCH3 3-thienyl radical H
857 OCH3 3-thienyl radical CH3
858 OCH3 3-thienyl radical C2H5
859 OCH3 3-thienyl radical n-C3H7
860 OCH3 3-thienyl radical i-C3H7
861 OCH3 2-oxazolyl radical H
862 OCH3 2-oxazolyl radical CH3
863 OCH3 2-oxazolyl radical C2H5
864 OCH3 2-oxazolyl radical n-C3H7
865 OCH3 2-oxazolyl radical i-C3H7
866 OCH3 4-oxazolyl radical H
867 OCH3 4-oxazolyl radical CH3
868 OCH3 4-oxazolyl radical C2H5
869 OCH3 4-oxazolyl radical n-C3H7
870 OCH3 4-oxazolyl radical i-C3H7
871 OCH3 2-thiazolyl group H
872 OCH3 2-thiazolyl group CH3
873 OCH3 2-thiazolyl group C2H5
874 OCH3 2-thiazolyl group n-C3H7
875 OCH3 2-thiazolyl group i-C3H7
876 OCH3 4-thiazolyl group H
877 OCH3 4-thiazolyl group CH3
No. R3 R4 R5
878 OCH3 4-thiazolyl group C2H5
879 OCH3 4-thiazolyl group n-C3H7
880 OCH3 4-thiazolyl group i-C3H7
881 OCH3 3-isoxazolyl H
882 OCH3 3-isoxazolyl CH3
883 OCH3 3-isoxazolyl C2H5
884 OCH3 3-isoxazolyl n-C3H7
885 OCH3 3-isoxazolyl i-C3H7
886 OCH3 5-isoxazolyl H
887 OCH3 5-isoxazolyl CH3
888 OCH3 5-isoxazolyl C2H5
889 OCH3 5-isoxazolyl n-C3H7
890 OCH3 5-isoxazolyl i-C3H7
891 OCH3 2-imidazolyl H
892 OCH3 2-imidazolyl CH3
893 OCH3 2-imidazolyl C2H5
894 OCH3 2-imidazolyl n-C3H7
895 OCH3 2-imidazolyl i-C3H7
896 OCH3 3-pyrazolyl radical H
897 OCH3 3-pyrazolyl radical CH3
898 OCH3 3-pyrazolyl radical C2H5
899 OCH3 3-pyrazolyl radical n-C3H7
900 OCH3 3-pyrazolyl radical i-C3H7
901 OCH3 4-pyrazolyl radical H
902 OCH3 4-pyrazolyl radical CH3
903 OCH3 4-pyrazolyl radical C2H5
904 OCH3 4-pyrazolyl radical n-C3H7
905 OCH3 4-pyrazolyl radical i-C3H7
906 OH H H
907 OH H CH3
908 OH H C2H5
909 OH H n-C3H7
910 OH H i-C3H7
911 OH OH H
912 OH OH CH3
913 OH OH C2H5
914 OH OH n-C3H7
No. R3 R4 R5
915 OH OH i-C3H7
916 OH Cl n-C4H9
917 OH Cl CH3
918 OH Cl C2H5
919 OH Cl n-C3H7
920 OH Cl i-C3H7
921 OH OCH3 H
922 OH OCH3 CH3
923 OH OCH3 C2H5
924 OH OCH3 n-C3H7
925 OH OCH3 i-C3H7
926 OH SCH3 H
927 OH SCH3 CH3
928 OH SCH3 C2H5
929 OH SCH3 n-C3H7
930 OH SCH3 i-C3H7
931 OH CH3 H
932 OH CH3 CH3
933 OH CH3 C2H5
934 OH CH3 n-C3H7
935 OH CH3 i-C3H7
936 OH Cyclopropyl group H
937 OH Cyclopropyl group CH3
938 OH Cyclopropyl group C2H5
939 OH Cyclopropyl group n-C3H7
940 OH Cyclopropyl group i-C3H7
941 OH 2-pyridyl group H
942 OH 2-pyridyl group CH3
943 OH 2-pyridyl group C2H5
944 OH 2-pyridyl group n-C3H7
945 OH 2-pyridyl group i-C3H7
946 OH 3-pyridyl group H
947 OH 3-pyridyl group CH3
948 OH 3-pyridyl group C2H5
949 OH 3-pyridyl group n-C3H7
950 OH 3-pyridyl group i-C3H7
951 OH 4-pyridyl group H
No. R3 R4 R5
952 OH 4-pyridyl group CH3
953 OH 4-pyridyl group C2H5
954 OH 4-pyridyl group n-C3H7
955 OH 4-pyridyl group i-C3H7
956 OH 2-pyrimidinyl radicals H
957 OH 2-pyrimidinyl radicals CH3
958 OH 2-pyrimidinyl radicals C2H5
959 OH 2-pyrimidinyl radicals n-C3H7
960 OH 2-pyrimidinyl radicals i-C3H7
961 OH 4-pyrimidinyl radicals H
962 OH 4-pyrimidinyl radicals CH3
963 OH 4-pyrimidinyl radicals C2H5
964 OH 4-pyrimidinyl radicals n-C3H7
965 OH 4-pyrimidinyl radicals i-C3H7
966 OH 5-pyrimidinyl radicals H
967 OH 5-pyrimidinyl radicals CH3
968 OH 5-pyrimidinyl radicals C2H5
969 OH 5-pyrimidinyl radicals n-C3H7
970 OH 5-pyrimidinyl radicals i-C3H7
971 OH 1, 3, 5-triazinyl H
972 OH 1, 3, 5-triazinyl CH3
973 OH 1, 3, 5-triazinyl C2H5
974 OH 1, 3, 5-triazinyl n-C3H7
975 OH 1, 3, 5-triazinyl i-C3H7
976 OH 2-furyl radical H
977 OH 2-furyl radical CH3
978 OH 2-furyl radical C2H5
979 OH 2-furyl radical n-C3H7
980 OH 2-furyl radical i-C3H7
981 OH 3-furyl radical H
982 OH 3-furyl radical CH3
983 OH 3-furyl radical C2H5
984 OH 3-furyl radical n-C3H7
985 OH 3-furyl radical i-C3H7
986 OH 2-thienyl radical H
987 OH 2-thienyl radical CH3
988 OH 2-thienyl radical C2H5
989 OH 2-thienyl radical n-C3H7
No. R3 R4 R5
990 OH 2-thienyl radical i-C3H7
991 OH 3-thienyl radical H
992 OH 3-thienyl radical CH3
993 OH 3-thienyl radical C2H5
994 OH 3-thienyl radical n-C3H7
995 OH 3-thienyl radical i-C3H7
996 OH 2-oxazolyl radical H
997 OH 2-oxazolyl radical CH3
998 OH 2-oxazolyl radical C2H5
999 OH 2-oxazolyl radical n-C3H7
1000 OH 2-oxazolyl radical i-C3H7
1001 OH 4-oxazolyl radical H
1002 OH 4-oxazolyl radical CH3
1003 OH 4-oxazolyl radical C2H5
1004 OH 4-oxazolyl radical n-C3H7
1005 OH 2-thiazolyl group i-C3H7
1006 OH 2-thiazolyl group H
1007 OH 2-thiazolyl group CH3
1008 OH 2-thiazolyl group C2H5
1009 OH 2-thiazolyl group n-C3H7
1010 OH 2-thiazolyl group i-C3H7
1011 OH 4-thiazolyl group H
1012 OH 4-thiazolyl group CH3
1013 OH 4-thiazolyl group C2H5
1014 OH 4-isoxazolyl n-C3H7
1015 OH 4-isoxazolyl i-C3H7
1016 OH 3-isoxazolyl H
1017 OH 3-isoxazolyl CH3
1018 OH 3-isoxazolyl C2H5
1019 OH 3-isoxazolyl n-C3H7
1020 OH 3-isoxazolyl i-C3H7
1021 OH 5-isoxazolyl H
1022 OH 5-isoxazolyl CH3
1023 OH 5-isoxazolyl C2H5
1024 OH 5-isoxazolyl n-C3H7
1025 OH 5-isoxazolyl i-C3H7
1026 OH 2-imidazolyl H
1027 OH 2-imidazolyl CH3
No. R3 R4 R5
1028 OH 2-imidazolyl C2H5
1029 OH 2-imidazolyl n-C3H7
1030 OH 2-imidazolyl i-C3H7
1031 OH 3-pyrazolyl radical H
1032 OH 3-pyrazolyl radical CH3
1033 OH 3-pyrazolyl radical C2H5
1034 OH 3-pyrazolyl radical n-C3H7
1035 OH 3-pyrazolyl radical i-C3H7
1036 OH 4-pyrazolyl radical H
1037 OH 4-pyrazolyl radical CH3
1038 OH 4-pyrazolyl radical C2H5
1039 OH 4-pyrazolyl radical n-C3H7
1040 OH 4-pyrazolyl radical i-C3H7
1041 H H H
1042 H H CH3
1043 H H C2H5
1044 H H n-C3H7
1045 H H i-C3H7
1046 H OH H
1047 H OH CH3
1048 H OH C2H5
1049 H OH n-C3H7
1050 H OH i-C3H7
1051 H Cl n-C4H9
1052 H Cl CH3
1053 H Cl C2H5
1054 H Cl n-C3H7
1055 H Cl i-C3H7
1056 H OCH3 H
1057 H OCH3 CH3
1058 H OCH3 C2H5
1059 H OCH3 n-C3H7
1060 H OCH3 i-C3H7
1061 H CH3 H
1062 H CH3 CH3
1063 H CH3 C2H5
1064 H CH3 n-C3H7
1065 H CH3 i-C3H7
No. R3 R4 R5
1066 H Cyclopropyl group H
1067 H Cyclopropyl group CH3
1068 H Cyclopropyl group C2H5
1069 H Cyclopropyl group n-C3H7
1070 H Cyclopropyl group i-C3H7
1071 Cl H H
1072 Cl H CH3
1073 Cl H C2H5
1074 Cl H n-C3H7
1075 Cl H i-C3H7
1076 Cl OH H
1077 Cl OH CH3
1078 Cl OH C2H5
1079 Cl OH n-C3H7
1080 Cl OH i-C3H7
1081 Cl Cl n-C4H9
1082 Cl Cl CH3
1083 Cl Cl C2H5
1084 Cl Cl n-C3H7
1085 Cl Cl i-C3H7
1086 Cl OCH3 H
1087 Cl OCH3 CH3
1088 Cl OCH3 C2H5
1089 Cl OCH3 n-C3H7
1090 Cl OCH3 i-C3H7
1091 Cl CH3 H
1092 Cl CH3 CH3
1093 Cl CH3 C2H5
1094 Cl CH3 n-C3H7
1095 Cl CH3 i-C3H7
1096 Cl Cyclopropyl group H
1097 Cl Cyclopropyl group CH3
1098 Cl Cyclopropyl group C2H5
1099 Cl Cyclopropyl group n-C3H7
1100 Cl Cyclopropyl group i-C3H7
1101 SCH3 H H
1102 SCH3 H CH3
1103 SCH3 H C2H5
No. R3 R4 R5
1104 SCH3 H n-C3H7
1105 SCH3 H i-C3H7
1106 SCH3 OH H
1107 SCH3 OH CH3
1108 SCH3 OH C2H5
1109 SCH3 OH n-C3H7
1110 SCH3 OH i-C3H7
1111 SCH3 CH3 H
1112 SCH3 CH3 CH3
1113 SCH3 CH3 C2H5
1114 SCH3 CH3 n-C3H7
1115 SCH3 CH3 i-C3H7
1116 SCH3 SCH3 H
1117 SCH3 SCH3 CH3
1118 SCH3 SCH3 C2H5
1119 SCH3 SCH3 n-C3H7
1120 SCH3 SCH3 i-C3H7
1121 SCH3 Cyclopropyl group H
1122 SCH3 Cyclopropyl group CH3
1123 SCH3 Cyclopropyl group C2H5
1124 SCH3 Cyclopropyl group n-C3H7
1125 SCH3 Cyclopropyl group i-C3H7
1126 Cyclo- propyl H H
1127 Cyclo- propyl H CH3
1128 Cyclo- propyl H C2H5
1129 Cyclopropyl group H n-C3H7
1130 Cyclopropyl group H i-C3H7
1131 Cyclopropyl group OH H
1132 Cyclopropyl group OH CH3
1133 Cyclopropyl group OH C2H5
1134 Cyclopropyl group OH n-C3H7
No. R3 R4 R5
1135 Cyclopropyl group OH i-C3H7
1136 Cyclopropyl group Cl n-C4H9
1137 Cyclopropyl group Cl CH3
1138 Cyclopropyl group Cl C2H5
1139 Cyclopropyl group Cl n-C3H7
1140 Cyclopropyl group Cl i-C3H7
1141 Cyclopropyl group OCH3 H
1142 Cyclopropyl group OCH3 CH3
1143 Cyclopropyl group OCH3 C2H5
1144 Cyclopropyl group OCH3 n-C3H7
1145 Cyclopropyl group OCH3 i-C3H7
1146 Cyclopropyl group SCH3 H
1147 Cyclopropyl group SCH3 CH3
1148 Cyclopropyl group SCH3 C2H5
1149 Cyclopropyl group SCH3 n-C3H7
1150 Cyclopropyl group SCH3 i-C3H7
1151 Cyclopropyl group CH3 H
1152 Cyclopropyl group CH3 CH3
1153 Cyclopropyl group CH3 C2H5
1154 Cyclopropyl group CH3 n-C3H7
1155 Cyclopropyl group CH3 i-C3H7
1156 CH3 2-F-C6H4 H
1157 CH3 2-F-C6H4 CH3
1158 CH3 2-F-C6H4 C2H5
No. R3 R4 R5
1159 CH3 2-F-C6H4 n-C3H7
1160 CH3 2-F-C6H4 i-C3H7
1161 CH3 2-F-C6H4 n-C4H9
1162 CH3 2-F-C6H4 t-C4H9
1163 CH3 2-F-C6H4 n-C6H13
1164 CH3 2-F-C6H4 Prop-1-en-3-yl
1165 CH3 2-F-C6H4 (E) -1-chloroprop-1-en-3-yl
1166 CH3 2-F-C6H4 Propin-3-yl
1167 CH3 2-F-C6H4 3-methyl-but-2-en-1-yl
1168 CH3 3-F-C6H4 H
1169 CH3 3-F-C6H4 CH3
1170 CH3 3-F-C6H4 C2H5
1171 CH3 3-F-C6H4 n-C3H7
1172 CH3 3-F-C6H4 i-C3H7
1173 CH3 3-F-C6H4 n-C4H9
1174 CH3 3-F-C6H4 t-C4H9
1175 CH3 3-F-C6H4 n-C6H13
1176 CH3 3-F-C6H4 Prop-1-en-3-yl
1177 CH3 3-F-C6H4 (E) -1-chloroprop-1-en-3-yl
1178 CH3 3-F-C6H4 Propin-3-yl
1179 CH3 3-F-C6H4 3-methyl-but-2-en-1-yl
1180 CH3 4-F-C6H4 H
1181 CH3 4-F-C6H4 CH3
1182 CH3 4-F-C6H4 C2H5
1183 CH3 4-F-C6H4 n-C3H7
1184 CH3 4-F-C6H4 i-C3H7
1185 CH3 4-F-C6H4 n-C4H9
1186 CH3 4-F-C6H4 t-C4H9
1187 CH3 4-F-C6H4 n-C6H13
1188 CH3 4-F-C6H4 Prop-1-en-3-yl
1189 CH3 4-F-C6H4 (E) -1-chloroprop-1-en-3-yl
1190 CH3 4-F-C6H4 Propin-3-yl
1191 CH3 4-F-C6H4 3-methyl-but-2-en-1-yl
1192 CH3 2-Cl-C6H4 H
1193 CH3 2-Cl-C6H4 CH3
1194 CH3 2-Cl-C6H4 C2H5
1195 CH3 2-Cl-C6H4 n-C3H7
1196 CH3 2-Cl-C6H4 i-C3H7
No. R3 R4 R5
1197 CH3 2-Cl-C6H4 n-C4H9
1198 CH3 2-Cl-C6H4 t-C4H9
1199 CH3 2-Cl-C6H4 n-C6H13
1200 CH3 2-Cl-C6H4 Prop-1-en-3-yl
1201 CH3 2-Cl-C6H4 (E) -1-chloroprop-1-en-3-yl
1202 CH3 2-Cl-C6H4 Propin-3-yl
1203 CH3 2-Cl-C6H4 3-methyl-but-2-en-1-yl
1204 CH3 3-Cl-C6H4 H
1205 CH3 3-Cl-C6H4 CH3
1206 CH3 3-Cl-C6H4 C2H5
1207 CH3 3-Cl-C6H4 n-C3H7
1208 CH3 3-Cl-C6H4 i-C3H7
1209 CH3 3-Cl-C6H4 n-C4H9
1210 CH3 3-Cl-C6H4 t-C4H9
1211 CH3 3-Cl-C6H4 n-C6H13
1212 CH3 3-Cl-C6H4 Prop-1-en-3-yl
1213 CH3 3-Cl-C6H4 (E) -1-chloroprop-1-en-3-yl
1214 CH3 3-Cl-C6H4 Propin-3-yl
1215 CH3 3-Cl-C6H4 3-methyl-but-2-en-1-yl
1216 CH3 4-Cl-C6H4 H
1217 CH3 4-Cl-C6H4 CH3
1218 CH3 4-Cl-C6H4 C2H5
1219 CH3 4-Cl-C6H4 n-C3H7
1220 CH3 4-Cl-C6H4 i-C3H7
1221 CH3 4-Cl-C6H4 n-C4H9
1222 CH3 4-Cl-C6H4 t-C4H9
1223 CH3 4-Cl-C6H4 n-C6H13
1224 CH3 4-Cl-C6H4 Prop-1-en-3-yl
1225 CH3 4-Cl-C6H4 (E) -1-chloroprop-1-en-3-yl
1226 CH3 4-Cl-C6H4 Propin-3-yl
1227 CH3 4-Cl-C6H4 3-methyl-but-2-en-1-yl
1228 CH3 2，3-Cl2-C6H3 H
1229 CH3 2，3-Cl2-C6H3 CH3
1230 CH3 2，3-Cl2-C6H3 C2H5
1231 CH3 2，3-Cl2-C6H3 n-C3H7
1232 CH3 2，3-Cl2-C6H3 i-C3H7
1233 CH3 2，3-Cl2-C6H3 n-C4H9
1234 CH3 2，3-Cl2-C6H3 t-C4H9
No. R3 R4 R5
1235 CH3 2，3-Cl2-C6H3 n-C6H13
1236 CH3 2，3-Cl2-C6H3 Prop-1-en-3-yl
1237 CH3 2，3-Cl2-C6H3 (E) -1-chloroprop-1-en-3-yl
1238 CH3 2，3-Cl2-C6H3 Propin-3-yl
1239 CH3 2，3-Cl2-C6H3 3-methyl-but-2-en-1-yl
1240 CH3 2，4-Cl2-C6H3 H
1241 CH3 2，4-Cl2-C6H3 CH3
1242 CH3 2，4-Cl2-C6H3 C2H5
1243 CH3 2，4-Cl2-C6H3 n-C3H7
1244 CH3 2，4-Cl2-C6H3 i-C3H7
1245 CH3 2，4-Cl2-C6H3 n-C4H9
1246 CH3 2，4-Cl2-C6H3 t-C4H9
1247 CH3 2，4-Cl2-C6H3 n-C6H13
1248 CH3 2，4-Cl2-C6H3 Prop-1-en-3-yl
1249 CH3 2，4-Cl2-C6H3 (E) -1-chloroprop-1-en-3-yl
1250 CH3 2，4-Cl2-C6H3 Propin-3-yl
1251 CH3 2，4-Cl2-C6H3 3-methyl-but-2-en-1-yl
1252 CH3 2，5-Cl2-C6H3 H
1253 CH3 2，5-Cl2-C6H3 CH3
1254 CH3 2，5-Cl2-C6H3 C2H5
1255 CH3 2，5-Cl2-C6H3 n-C3H7
1256 CH3 2，5-Cl2-C6H3 i-C3H7
1257 CH3 2，5-Cl2-C6H3 n-C4H9
1258 CH3 2，5-Cl2-C6H3 t-C4H9
1259 CH3 2，5-Cl2-C6H3 n-C6H13
1260 CH3 2，5-Cl2-C6H3 Prop-1-en-3-yl
1261 CH3 2，5-Cl2-C6H3 (E) -1-chloroprop-1-en-3-yl
1262 CH3 2，5-Cl2-C6H3 Propin-3-yl
1263 CH3 2，5-Cl2-C6H3 3-methyl-but-2-en-1-yl
1264 CH3 2，6-Cl2-C6H3 H
1265 CH3 2，6-Cl2-C6H3 CH3
1266 CH3 2，6-Cl2-C6H3 C2H5
1267 CH3 2，6-Cl2-C6H3 n-C3H7
1268 CH3 2，6-Cl2-C6H3 i-C3H7
1269 CH3 2，6-Cl2-C6H3 n-C4H9
1270 CH3 2，6-Cl2-C6H3 t-C4H9
1271 CH3 2，6-Cl2-C6H3 n-C6H13
1272 CH3 2，6-Cl2-C6H3 Prop-1-en-3-yl
No. R3 R4 R5
1273 CH3 2，6-Cl2-C6H3 (E) -1-chloroprop-1-en-3-yl
1274 CH3 2，6-Cl2-C6H3 Propin-3-yl
1275 CH3 2，6-Cl2-C6H3 3-methyl-but-2-en-1-yl
1276 CH3 3，4-Cl2-C6H3 H
1277 CH3 3，4-Cl2-C6H3 CH3
1278 CH3 3，4-Cl2-C6H3 C2H5
1279 CH3 3，4-Cl2-C6H3 n-C3H7
1280 CH3 3，4-Cl2-C6H3 i-C3H7
1281 CH3 3，4-Cl2-C6H3 n-C4H9
1282 CH3 3，4-Cl2-C6H3 t-C4H9
1283 CH3 3，4-Cl2-C6H3 n-C6H13
1284 CH3 3，4-Cl2-C6H3 Prop-1-en-3-yl
1285 CH3 3，4-Cl2-C6H3 (E) -1-chloroprop-1-en-3-yl
1286 CH3 3，4-Cl2-C6H3 Propin-3-yl
1287 CH3 3，4-Cl2-C6H3 3-methyl-but-2-en-1-yl
1288 CH3 3，5-Cl2-C6H3 H
1289 CH3 3，5-Cl2-C6H3 CH3
1290 CH3 3，5-Cl2-C6H3 C2H5
1291 CH3 3，5-Cl2-C6H3 n-C3H7
1292 CH3 3，5-Cl2-C6H3 i-C3H7
1293 CH3 3，5-Cl2-C6H3 n-C4H9
1294 CH3 3，5-Cl2-C6H3 t-C4H9
1295 CH3 3，5-Cl2-C6H3 n-C6H13
1296 CH3 3，5-Cl2-C6H3 Prop-1-en-3-yl
1297 CH3 3，5-Cl2-C6H3 (E) -1-chloroprop-1-en-3-yl
1298 CH3 3，5-Cl2-C6H3 Propin-3-yl
1299 CH3 3，5-Cl2-C6H3 3-methyl-but-2-en-1-yl
1300 CH3 2-Br-C6H4 H
1301 CH3 2-Br-C6H4 CH3
1302 CH3 2-Br-C6H4 C2H5
1303 CH3 2-Br-C6H4 n-C3H7
1304 CH3 2-Br-C6H4 i-C3H7
1305 CH3 2-Br-C6H4 n-C4H9
1306 CH3 2-Br-C6H4 t-C4H9
1307 CH3 2-Br-C6H4 n-C6H13
1308 CH3 2-Br-C6H4 Prop-1-en-3-yl
1309 CH3 2-Br-C6H4 (E) -1-chloroprop-1-en-3-yl
1310 CH3 2-Br-C6H4 Propin-3-yl
No. R3 R4 R5
1311 CH3 2-Br-C6H4 3-methyl-but-2-en-1-yl
1312 CH3 3-Br-C6H4 H
1313 CH3 3-Br-C6H4 CH3
1314 CH3 3-Br-C6H4 C2H5
1315 CH3 3-Br-C6H4 n-C3H7
1316 CH3 3-Br-C6H4 i-C3H7
1317 CH3 3-Br-C6H4 n-C4H9
1318 CH3 3-Br-C6H4 t-C4H9
1319 CH3 3-Br-C6H4 n-C6H13
1320 CH3 3-Br-C6H4 Prop-1-en-3-yl
1321 CH3 3-Br-C6H4 (E) -1-chloroprop-1-en-3-yl
1322 CH3 3-Br-C6H4 Propin-3-yl
1323 CH3 3-Br-C6H4 3-methyl-but-2-en-1-yl
1324 CH3 4-Br-C6H4 H
1325 CH3 4-Br-C6H4 CH3
1326 CH3 4-Br-C6H4 C2H5
1327 CH3 4-Br-C6H4 n-C3H7
1328 CH3 4-Br-C6H4 i-C3H7
1329 CH3 4-Br-C6H4 n-C4H9
1330 CH3 4-Br-C6H4 t-C4H9
1331 CH3 4-Br-C6H4 n-C6H13
1332 CH3 4-Br-C6H4 Prop-1-en-3-yl
1333 CH3 4-Br-C6H4 (E) -1-chloroprop-1-en-3-yl
1334 CH3 4-Br-C6H4 Propin-3-yl
1335 CH3 4-Br-C6H4 3-methyl-but-2-en-1-yl
1336 CH3 2-I-C6H4 H
1337 CH3 2-I-C6H4 CH3
1338 CH3 2-I-C6H4 C2H5
1339 CH3 2-I-C6H4 n-C3H7
1340 CH3 2-I-C6H4 i-C3H7
1341 CH3 2-I-C6H4 n-C4H9
1342 CH3 2-I-C6H4 t-C4H9
1343 CH3 2-I-C6H4 n-C6H13
1344 CH3 2-I-C6H4 Prop-1-en-3-yl
1345 CH3 2-I-C6H4 (E) -1-chloroprop-1-en-3-yl
1346 CH3 2-I-C6H4 Propin-3-yl
1347 CH3 2-I-C6H4 3-methyl-but-2-en-1-yl
1348 CH3 3-I-C6H4 H
No. R3 R4 R5
1349 CH3 3-I-C6H4 CH3
1350 CH3 3-I-C6H4 C2H5
1351 CH3 3-I-C6H4 n-C3H7
1352 CH3 3-I-C6H4 i-C3H7
1353 CH3 3-I-C6H4 n-C4H9
1354 CH3 3-I-C6H4 t-C4H9
1355 CH3 3-I-C6H4 n-C6H13
1356 CH3 3-I-C6H4 Prop-1-en-3-yl
1357 CH3 3-I-C6H4 (E) -1-chloroprop-1-en-3-yl
1358 CH3 3-I-C6H4 Propin-3-yl
1359 CH3 3-I-C6H4 3-methyl-but-2-en-1-yl
1360 CH3 4-I-C6H4 H
1361 CH3 4-I-C6H4 CH3
1362 CH3 4-I-C6H4 C2H5
1363 CH3 4-I-C6H4 n-C3H7
1364 CH3 4-I-C6H4 i-C3H7
1365 CH3 4-I-C6H4 n-C4H9
1366 CH3 4-I-C6H4 t-C4H9
1367 CH3 4-I-C6H4 n-C6H13
1368 CH3 4-I-C6H4 Prop-1-en-3-yl
1369 CH3 4-I-C6H4 (E) -1-chloroprop-1-en-3-yl
1370 CH3 4-I-C6H4 Propin-3-yl
1371 CH3 4-I-C6H4 3-methyl-but-2-en-1-yl
1372 CH3 2-CN-C6H4 H
1373 CH3 2-CN-C6H4 CH3
1374 CH3 2-CN-C6H4 C2H5
1375 CH3 2-CN-C6H4 n-C3H7
1376 CH3 2-CN-C6H4 i-C3H7
1377 CH3 2-CN-C6H4 n-C4H9
1378 CH3 2-CN-C6H4 t-C4H9
1379 CH3 2-CN-C6H4 n-C6H13
1380 CH3 2-CN-C6H4 Prop-1-en-3-yl
1381 CH3 2-CN-C6H4 (E) -1-chloroprop-1-en-3-yl
1382 CH3 2-CN-C6H4 Propin-3-yl
1383 CH3 2-CN-C6H4 3-methyl-but-2-en-1-yl
1384 CH3 3-CN-C6H4 H
1385 CH3 3-CN-C6H4 CH3
1386 CH3 3-CN-C6H4 C2H5
No. R3 R4 R5
1387 CH3 3-CN-C6H4 n-C3H7
1388 CH3 3-CN-C6H4 i-C3H7
1389 CH3 3-CN-C6H4 n-C4H9
1390 CH3 3-CN-C6H4 t-C4H9
1391 CH3 3-CN-C6H4 n-C6H13
1392 CH3 3-CN-C6H4 Prop-1-en-3-yl
1393 CH3 3-CN-C6H4 (E) -1-chloroprop-1-en-3-yl
1394 CH3 3-CN-C6H4 Propin-3-yl
1395 CH3 3-CN-C6H4 3-methyl-but-2-en-1-yl
1396 CH3 4-CN-C6H4 H
1397 CH3 4-CN-C6H4 CH3
1398 CH3 4-CN-C6H4 C2H5
1399 CH3 4-CN-C6H4 n-C3H7
1400 CH3 4-CN-C6H4 i-C3H7
1401 CH3 4-CN-C6H4 n-C4H9
1402 CH3 4-CN-C6H4 t-C4H9
1403 CH3 4-CN-C6H4 n-C6H13
1404 CH3 4-CN-C6H4 Prop-1-en-3-yl
1405 CH3 4-CN-C6H4 (E) -1-chloroprop-1-en-3-yl
1406 CH3 4-CN-C6H4 Propin-3-yl
1407 CH3 4-CN-C6H4 3-methyl-but-2-en-1-yl
1408 CH3 2-NO2-C6H4 H
1409 CH3 2-NO2-C6H4 CH3
1410 CH3 2-NO2-C6H4 C2H5
1411 CH3 2-NO2-C6H4 n-C3H7
1412 CH3 2-NO2-C6H4 i-C3H7
1413 CH3 2-NO2-C6H4 n-C4H9
1414 CH3 2-NO2-C6H4 t-C4H9
1415 CH3 2-NO2-C6H4 n-C6H13
1416 CH3 2-NO2-C6H4 Prop-1-en-3-yl
1417 CH3 2-NO2-C6H4 (E) -1-chloroprop-1-en-3-yl
1418 CH3 2-NO2-C6H4 Propin-3-yl
1419 CH3 2-NO2-C6H4 3-methyl-but-2-en-1-yl
1420 CH3 3-NO2-C6H4 H
1421 CH3 3-NO2-C6H4 CH3
1422 CH3 3-NO2-C6H4 C2H5
1423 CH3 3-NO2-C6H4 n-C3H7
1424 CH3 3-NO2-C6H4 i-C3H7
No. R3 R4 R5
1425 CH3 3-NO2-C6H4 n-C4H9
1426 CH3 3-NO2-C6H4 t-C4H9
1427 CH3 3-NO2-C6H4 n-C6H13
1428 CH3 3-NO2-C6H4 Prop-1-en-3-yl
1429 CH3 3-NO2-C6H4 (E) -1-chloroprop-1-en-3-yl
1430 CH3 3-NO2-C6H4 Propin-3-yl
1431 CH3 3-NO2-C6H4 3-methyl-but-2-en-1-yl
1432 CH3 4-NO2-C6H4 H
1433 CH3 4-NO2-C6H4 CH3
1434 CH3 4-NO2-C6H4 C2H5
1435 CH3 4-NO2-C6H4 n-C3H7
1436 CH3 4-NO2-C6H4 i-C3H7
1437 CH3 4-NO2-C6H4 n-C4H9
1438 CH3 4-NO2-C6H4 t-C4H9
1439 CH3 4-NO2-C6H4 n-C6H13
1440 CH3 4-NO2-C6H4 Prop-1-en-3-yl
1441 CH3 4-NO2-C6H4 (E) -1-chloroprop-1-en-3-yl
1442 CH3 4-NO2-C6H4 Propin-3-yl
1443 CH3 4-NO2-C6H4 3-methyl-but-2-en-1-yl
1444 CH3 2-CH3-C6H4 H
1445 CH3 2-CH3-C6H4 CH3
1446 CH3 2-CH3-C6H4 C2H5
1447 CH3 2-CH3-C6H4 n-C3H7
1448 CH3 2-CH3-C6H4 i-C3H7
1449 CH3 2-CH3-C6H4 n-C4H9
1450 CH3 2-CH3-C6H4 t-C4H9
1451 CH3 2-CH3-C6H4 n-C6H13
1452 CH3 2-CH3-C6H4 Prop-1-en-3-yl
1453 CH3 2-CH3-C6H4 (E) -1-chloroprop-1-en-3-yl
1454 CH3 2-CH3-C6H4 Propin-3-yl
1455 CH3 2-CH3-C6H4 3-methyl-but-2-en-1-yl
1456 CH3 3-CH3-C6H4 H
1457 CH3 3-CH3-C6H4 CH3
1458 CH3 3-CH3-C6H4 C2H5
1459 CH3 3-CH3-C6H4 n-C3H7
1460 CH3 3-CH3-C6H4 i-C3H7
1461 CH3 3-CH3-C6H4 n-C4H9
1462 CH3 3-CH3-C6H4 t-C4H9
No. R3 R4 R5
1463 CH3 3-CH3-C6H4 n-C6H13
1464 CH3 3-CH3-C6H4 Prop-1-en-3-yl
1465 CH3 3-CH3-C6H4 (E) -1-chloroprop-1-en-3-yl
1466 CH3 3-CH3-C6H4 Propin-3-yl
1467 CH3 3-CH3-C6H4 3-methyl-but-2-en-1-yl
1468 CH3 4-CH3-C6H4 H
1469 CH3 4-CH3-C6H4 CH3
1470 CH3 4-CH3-C6H4 C2H5
1471 CH3 4-CH3-C6H4 n-C3H7
1472 CH3 4-CH3-C6H4 i-C3H7
1473 CH3 4-CH3-C6H4 n-C4H9
1474 CH3 4-CH3-C6H4 t-C4H9
1475 CH3 4-CH3-C6H4 n-C6H13
1476 CH3 4-CH3-C6H4 Prop-1-en-3-yl
1477 CH3 4-CH3-C6H4 (E) -1-chloroprop-1-en-3-yl
1478 CH3 4-CH3-C6H4 Propyn-3-y
1479 CH3 4-CH3-C6H4 3-methyl-but-2-en-1-yl
1480 CH3 2，3-(CH3)2-C6H3 H
1481 CH3 2，3-(CH3)2-C6H3 CH3
1482 CH3 2，3-(CH3)2-C6H3 C2H5
1483 CH3 2，3-(CH3)2-C6H3 n-C3H7
1484 CH3 2，3-(CH3)2-C6H3 i-C3H7
1485 CH3 2，3-(CH3)2-C6H3 n-C4H9
1486 CH3 2，3-(CH3)2-C6H3 t-C4H9
1487 CH3 2，3-(CH3)2-C6H3 n-C6H13
1488 CH3 2，3-(CH3)2-C6H3 Prop-1-en-3-yl
1489 CH3 2，3-(CH3)2-C6H3 (E) -1-chloroprop-1-en-3-yl
1490 CH3 2，3-(CH3)2-C6H3 Propin-3-yl
1491 CH3 2，3-(CH3)2-C6H3 3-methyl-but-2-en-1-yl
1492 CH3 2，4-(CH3)2-C6H3 H
1493 CH3 2，4-(CH3)2-C6H3 CH3
1494 CH3 2，4-(CH3)2-C6H3 C2H5
1495 CH3 2，4-(CH3)2-C6H3 n-C3H7
1496 CH3 2，4-(CH3)2-C6H3 i-C3H7
1497 CH3 2，4-(CH3)2-C6H3 n-C4H9
1498 CH3 2，4-(CH3)2-C6H3 t-C4H9
1499 CH3 2，4-(CH3)2-C6H3 n-C6H13
1500 CH3 2，4-(CH3)2-C6H3 Prop-1-en-3-yl
No. R3 R4 R5
1501 CH3 2，4-(CH3)2-C6H3 (E) -1-chloroprop-1-en-3-yl
1502 CH3 2，4-(CH3)2-C6H3 Propin-3-yl
1503 CH3 2，4-(CH3)2-C6H3 3-methyl-but-2-en-1-yl
1504 CH3 2，5-(CH3)2-C6H3 H
1505 CH3 2，5-(CH3)2-C6H3 CH3
1506 CH3 2，5-(CH3)2-C6H3 C2H5
1507 CH3 2，5-(CH3)2-C6H3 n-C3H7
1508 CH3 2，5-(CH3)2-C6H3 i-C3H7
1509 CH3 2，5-(CH3)2-C6H3 n-C4H9
1510 CH3 2，5-(CH3)2-C6H3 t-C4H9
1511 CH3 2，5-(CH3)2-C6H3 n-C6H13
1512 CH3 2，5-(CH3)2-C6H3 Prop-1-en-3-yl
1513 CH3 2，5-(CH3)2-C6H3 (E) -1-chloroprop-1-en-3-yl
1514 CH3 2，5-(CH3)2-C6H3 Propin-3-yl
1515 CH3 2，5-(CH3)2-C6H3 3-methyl-but-2-en-1-yl
1516 CH3 2，6-(CH3)2-C6H3 H
1517 CH3 2，6-(CH3)2-C6H3 CH3
1518 CH3 2，6-(CH3)2-C6H3 C2H5
1519 CH3 2，6-(CH3)2-C6H3 n-C3H7
1520 CH3 2，6-(CH3)2-C6H3 i-C3H7
1521 CH3 2，6-(CH3)2-C6H3 n-C4H9
1522 CH3 2，6-(CH3)2-C6H3 t-C4H9
1523 CH3 2，6-(CH3)2-C6H3 n-C6H13
1524 CH3 2，6-(CH3)2-C6H3 Prop-1-en-3-yl
1525 CH3 2，6-(CH3)2-C6H3 (E) -1-chloroprop-1-en-3-yl
1526 CH3 2，6-(CH3)2-C6H3 Propin-3-yl
1527 CH3 2，6-(CH3)2-C6H3 3-methyl-but-2-en-1-yl
1528 CH3 3，4-(CH3)2-C6H3 H
1529 CH3 3，4-(CH3)2-C6H3 CH3
1530 CH3 3，4-(CH3)2-C6H3 C2H5
1531 CH3 3，4-(CH3)2-C6H3 n-C3H7
1532 CH3 3，4-(CH3)2-C6H3 i-C3H7
1533 CH3 3，4-(CH3)2-C6H3 n-C4H9
1534 CH3 3，4-(CH3)2-C6H3 t-C4H9
1535 CH3 3，4-(CH3)2-C6H3 n-C6H13
1536 CH3 3，4-(CH3)2-C6H3 Prop-1-en-3-yl
1537 CH3 3，4-(CH3)2-C6H3 (E) -1-chloroprop-1-en-3-yl
1538 CH3 3，4-(CH3)2-C6H3 Propin-3-yl
No. R3 R4 R5
1539 CH3 3，4-(CH3)2-C6H3 3-methyl-but-2-en-1-yl
1540 CH3 3，5-(CH3)2-C6H3 H
1541 CH3 3，5-(CH3)2-C6H3 CH3
1542 CH3 3，5-(CH3)2-C6H3 C2H5
1543 CH3 3，5-(CH3)2-C6H3 n-C3H7
1544 CH3 3，5-(CH3)2-C6H3 i-C3H7
1545 CH3 3，5-(CH3)2-C6H3 n-C4H9
1546 CH3 3，5-(CH3)2-C6H3 t-C4H9
1547 CH3 3，5-(CH3)2-C6H3 n-C6H13
1548 CH3 3，5-(CH3)2-C6H3 Prop-1-en-3-yl
1549 CH3 3，5-(CH3)2-C6H3 (E) -1-chloroprop-1-en-3-yl
1550 CH3 3，5-(CH3)2-C6H3 Propin-3-yl
1551 CH3 3，5-(CH3)2-C6H3 3-methyl-but-2-en-1-yl
1552 CH3 2-C2H5-C6H4 H
1553 CH3 2-C2H5-C6H4 CH3
1554 CH3 2-C2H5-C6H4 C2H5
1555 CH3 2-C2H5-C6H4 n-C3H7
1556 CH3 2-C2H5-C6H4 i-C3H7
1557 CH3 2-C2H5-C6H4 n-C4H9
1558 CH3 2-C2H5-C6H4 t-C4H9
1559 CH3 2-C2H5-C6H4 n-C6H13
1560 CH3 2-C2H5-C6H4 Prop-1-en-3-yl
1561 CH3 2-C2H5-C6H4 (E) -1-chloroprop-1-en-3-yl
1562 CH3 2-C2H5-C6H4 Propin-3-yl
1563 CH3 2-C2H5-C6H4 3-methyl-but-2-en-1-yl
1564 CH3 3-C2H5-C6H4 H
1565 CH3 3-C2H5-C6H4 CH3
1566 CH3 3-C2H5-C6H4 C2H5
1567 CH3 3-C2H5-C6H4 n-C3H7
1568 CH3 3-C2H5-C6H4 i-C3H7
1569 CH3 3-C2H5-C6H4 n-C4H9
1570 CH3 3-C2H5-C6H4 t-C4H9
1571 CH3 3-C2H5-C6H4 n-C6H13
1572 CH3 3-C2H5-C6H4 Prop-1-en-3-yl
1573 CH3 3-C2H5-C6H4 (E) -1-chloroprop-1-en-3-yl
1574 CH3 3-C2H5-C6H4 Propin-3-yl
1575 CH3 3-C2H5-C6H4 3-methyl-but-2-en-1-yl
1576 CH3 4-C2H5-C6H4 H
No. R3 R4 R5
1577 CH3 4-C2H5-C6H4 CH3
1578 CH3 4-C2H5-C6H4 C2H5
1579 CH3 4-C2H5-C6H4 n-C3H7
1580 CH3 4-C2H5-C6H4 i-C3H7
1581 CH3 4-C2H5-C6H4 n-C4H9
1582 CH3 4-C2H5-C6H4 t-C4H9
1583 CH3 4-C2H5-C6H4 n-C6H13
1584 CH3 4-C2H5-C6H4 Prop-1-en-3-yl
1585 CH3 4-C2H5-C6H4 (E) -1-chloroprop-1-en-3-yl
1586 CH3 4-C2H5-C6H4 Propin-3-yl
1587 CH3 4-C2H5-C6H4 3-methyl-but-2-en-1-yl
1588 CH3 2-i-C3H7-C6H4 H
1589 CH3 2-i-C3H7-C6H4 CH3
1590 CH3 2-i-C3H7-C6H4 C2H5
1591 CH3 2-i-C3H7-C6H4 n-C3H7
1592 CH3 2-i-C3H7-C6H4 i-C3H7
1593 CH3 2-i-C3H7-C6H4 n-C4H9
1594 CH3 2-i-C3H7-C6H4 t-C4H9
1595 CH3 2-i-C3H7-C6H4 n-C6H13
1596 CH3 2-i-C3H7-C6H4 Prop-1-en-3-yl
1597 CH3 2-i-C3H7-C6H4 (E) -1-chloroprop-1-en-3-yl
1598 CH3 2-i-C3H7-C6H4 Propin-3-yl
1599 CH3 2-i-C3H7-C6H4 3-methyl-but-2-en-1-yl
1600 CH3 3-i-C3H7-C6H4 H
1601 CH3 3-i-C3H7-C6H4 CH3
1602 CH3 3-i-C3H7-C6H4 C2H5
1603 CH3 3-i-C3H7-C6H4 n-C3H7
1604 CH3 3-i-C3H7-C6H4 i-C3H7
1605 CH3 3-i-C3H7-C6H4 n-C4H9
1606 CH3 3-i-C3H7-C6H4 t-C4H9
1607 CH3 3-i-C3H7-C6H4 n-C6H13
1608 CH3 3-i-C3H7-C6H4 Prop-1-en-3-yl
1609 CH3 3-i-C3H7-C6H4 (E) -1-chloroprop-1-en-3-yl
1610 CH3 3-i-C3H7-C6H4 Propin-3-yl
1611 CH3 3-i-C3H7-C6H4 3-methyl-but-2-en-1-yl
1612 CH3 4-i-C3H7-C6H4 H
1613 CH3 4-i-C3H7-C6H4 CH3
1614 CH3 4-i-C3H7-C6H4 C2H5
No. R3 R4 R5
1615 CH3 4-i-C3H7-C6H4 n-C3H7
1616 CH3 4-i-C3H7-C6H4 i-C3H7
1617 CH3 4-i-C3H7-C6H4 n-C4H9
1618 CH3 4-i-C3H7-C6H4 t-C4H9
1619 CH3 4-i-C3H7-C6H4 n-C6H13
1620 CH3 4-i-C3H7-C6H4 Prop-1-en-3-yl
1621 CH3 4-i-C3H7-C6H4 (E) -1-chloroprop-1-en-3-yl
1622 CH3 4-i-C3H7-C6H4 Propin-3-yl
1623 CH3 4-i-C3H7-C6H4 3-methyl-but-2-en-1-yl
1624 CH3 2-OH-C6H4 H
1625 CH3 2-OH-C6H4 CH3
1626 CH3 2-OH-C6H4 C2H5
1627 CH3 2-OH-C6H4 n-C3H7
1628 CH3 2-OH-C6H4 i-C3H7
1629 CH3 2-OH-C6H4 n-C4H9
1630 CH3 2-OH-C6H4 t-C4H9
1631 CH3 2-OH-C6H4 n-C6H13
1632 CH3 2-OH-C6H4 Prop-1-en-3-yl
1633 CH3 2-OH-C6H4 (E) -1-chloroprop-1-en-3-yl
1634 CH3 2-OH-C6H4 Propin-3-yl
1635 CH3 2-OH-C6H4 3-methyl-but-2-en-1-yl
1636 CH3 3-OH-C6H4 H
1637 CH3 3-OH-C6H4 CH3
1638 CH3 3-OH-C6H4 C2H5
1639 CH3 3-OH-C6H4 n-C3H7
1640 CH3 3-OH-C6H4 i-C3H7
1641 CH3 3-OH-C6H4 n-C4H9
1642 CH3 3-OH-C6H4 t-C4H9
1643 CH3 3-OH-C6H4 n-C6H13
1644 CH3 3-OH-C6H4 Prop-1-en-3-yl
1645 CH3 3-OH-C6H4 (E) -1-chloroprop-1-en-3-yl
1646 CH3 3-OH-C6H4 Propin-3-yl
1647 CH3 3-OH-C6H4 3-methyl-but-2-en-1-yl
1648 CH3 4-OH-C6H4 H
1649 CH3 4-OH-C6H4 CH3
1650 CH3 4-OH-C6H4 C2H5
1651 CH3 4-OH-C6H4 n-C3H7
1652 CH3 4-OH-C6H4 i-C3H7
No. R3 R4 R5
1653 CH3 4-OH-C6H4 n-C4H9
1654 CH3 4-OH-C6H4 t-C4H9
1655 CH3 4-OH-C6H4 n-C6H13
1656 CH3 4-OH-C6H4 Prop-1-en-3-yl
1657 CH3 4-OH-C6H4 (E) -1-chloroprop-1-en-3-yl
1658 CH3 4-OH-C6H4 Propin-3-yl
1659 CH3 4-OH-C6H4 3-methyl-but-2-en-1-yl
1660 CH3 2-OCH3-C6H4 H
1661 CH3 2-OCH3-C6H4 CH3
1662 CH3 2-OCH3-C6H4 C2H5
1663 CH3 2-OCH3-C6H4 n-C3H7
1664 CH3 2-OCH3-C6H4 i-C3H7
1665 CH3 2-OCH3-C6H4 n-C4H9
1666 CH3 2-OCH3-C6H4 t-C4H9
1667 CH3 2-OCH3-C6H4 n-C6H13
1668 CH3 2-OCH3-C6H4 Prop-1-en-3-yl
1669 CH3 2-OCH3-C6H4 (E) -1-chloroprop-1-en-3-yl
1670 CH3 2-OCH3-C6H4 Propin-3-yl
1671 CH3 2-OCH3-C6H4 3-methyl-but-2-en-1-yl
1672 CH3 3-OCH3-C6H4 H
1673 CH3 3-OCH3-C6H4 CH3
1674 CH3 3-OCH3-C6H4 C2H5
1675 CH3 3-OCH3-C6H4 n-C3H7
1676 CH3 3-OCH3-C6H4 i-C3H7
1677 CH3 3-OCH3-C6H4 n-C4H9
1678 CH3 3-OCH3-C6H4 t-C4H9
1679 CH3 3-OCH3-C6H4 n-C6H13
1680 CH3 3-OCH3-C6H4 Prop-1-en-3-yl
1681 CH3 3-OCH3-C6H4 (E) -1-chloroprop-1-en-3-yl
1682 CH3 3-OCH3-C6H4 Propin-3-yl
1683 CH3 3-OCH3-C6H4 3-methyl-but-2-en-1-yl
1684 CH3 4-OCH3-C6H4 H
1685 CH3 4-OCH3-C6H4 CH3
1686 CH3 4-OCH3-C6H4 C2H5
1687 CH3 4-OCH3-C6H4 n-C3H7
1688 CH3 4-OCH3-C6H4 i-C3H7
1689 CH3 4-OCH3-C6H4 n-C4H9
1690 CH3 4-OCH3-C6H4 t-C4H9
No. R3 R4 R5
1691 CH3 4-OCH3-C6H4 n-C6H13
1692 CH3 4-OCH3-C6H4 Prop-1-en-3-yl
1693 CH3 4-OCH3-C6H4 (E) -1-chloroprop-1-en-3-yl
1694 CH3 4-OCH3-C6H4 Propin-3-yl
1695 CH3 4-OCH3-C6H4 3-methyl-but-2-en-1-yl
1696 CH3 2-OC2H5-C6H4 H
1697 CH3 2-OC2H5-C6H4 CH3
1698 CH3 2-OC2H5-C6H4 C2H5
1699 CH3 2-OC2H5-C6H4 n-C3H7
1700 CH3 2-OC2H5-C6H4 i-C3H7
1701 CH3 2-OC2H5-C6H4 n-C4H9
1702 CH3 2-OC2H5-C6H4 t-C4H9
1703 CH3 2-OC2H5-C6H4 n-C6H13
1704 CH3 2-OC2H5-C6H4 Prop-1-en-3-yl
1705 CH3 2-OC2H5-C6H4 (E) -1-chloroprop-1-en-3-yl
1706 CH3 2-OC2H5-C6H4 Propin-3-yl
1707 CH3 2-OC2H5-C6H4 3-methyl-but-2-en-1-yl
1708 CH3 3-OC2H5-C6H4 H
1709 CH3 3-OC2H5-C6H4 CH3
1710 CH3 3-OC2H5-C6H4 C2H5
1711 CH3 3-OC2H5-C6H4 n-C3H7
1712 CH3 3-OC2H5-C6H4 i-C3H7
1713 CH3 3-OC2H5-C6H4 n-C4H9
1714 CH3 3-OC2H5-C6H4 t-C4H9
1715 CH3 3-OC2H5-C6H4 n-C6H13
1716 CH3 3-OC2H5-C6H4 Prop-1-en-3-yl
1717 CH3 3-OC2H5-C6H4 (E) -1-chloroprop-1-en-3-yl
1718 CH3 3-OC2H5-C6H4 Propin-3-yl
1719 CH3 3-OC2H5-C6H4 3-methyl-but-2-en-1-yl
1720 CH3 4-OC2H5-C6H4 H
1721 CH3 4-OC2H5-C6H4 CH3
1722 CH3 4-OC2H5-C6H4 C2H5
1723 CH3 4-OC2H5-C6H4 n-C3H7
1724 CH3 4-OC2H5-C6H4 i-C3H7
1725 CH3 4-OC2H5-C6H4 n-C4H9
1726 CH3 4-OC2H5-C6H4 t-C4H9
1727 CH3 4-OC2H5-C6H4 n-C6H13
1728 CH3 4-OC2H5-C6H4 Prop-1-en-3-yl
No. R3 R4 R5
1729 CH3 4-OC2H5-C6H4 (E) -1-chloroprop-1-en-3-yl
1730 CH3 4-OC2H5-C6H4 Propin-3-yl
1731 CH3 4-OC2H5-C6H4 3-methyl-but-2-en-1-yl
1732 CH3 2-O-(i-C3H7)-C6H4 H
1733 CH3 2-O-(i-C3H7)-C6H4 CH3
1734 CH3 2-O-(i-C3H7)-C6H4 C2H5
1735 CH3 2-O-(i-C3H7)-C6H4 n-C3H7
1736 CH3 2-O-(i-C3H7)-C6H4 i-C3H7
1737 CH3 2-O-(i-C3H7)-C6H4 n-C4H9
1738 CH3 2-O-(i-C3H7)-C6H4 t-C4H9
1739 CH3 2-O-(i-C3H7)-C6H4 n-C6H13
1740 CH3 2-O-(i-C3H7)-C6H4 Prop-1-en-3-yl
1741 CH3 2-O-(i-C3H7)-C6H4 (E) -1-chloroprop-1-en-3-yl
1742 CH3 2-O-(i-C3H7)-C6H4 Propin-3-yl
1743 CH3 2-O-(i-C3H7)-C6H4 3-methyl-but-2-en-1-yl
1744 CH3 3-O-(i-C3H7)-C6H4 H
1745 CH3 3-O-(i-C3H7)-C6H4 CH3
1746 CH3 3-O-(i-C3H7)-C6H4 C2H5
1747 CH3 3-O-(i-C3H7)-C6H4 n-C3H7
1748 CH3 3-O-(i-C3H7)-C6H4 i-C3H7
1749 CH3 3-O-(i-C3H7)-C6H4 n-C4H9
1750 CH3 3-O-(i-C3H7)-C6H4 t-C4H9
1751 CH3 3-O-(i-C3H7)-C6H4 n-C6H13
1752 CH3 3-O-(i-C3H7)-C6H4 Prop-1-en-3-yl
1753 CH3 3-O-(i-C3H7)-C6H4 (E) -1-chloroprop-1-en-3-yl
1754 CH3 3-O-(i-C3H7)-C6H4 Propin-3-yl
1755 CH3 3-O-(i-C3H7)-C6H4 3-methyl-but-2-en-1-yl
1756 CH3 4-O-(i-C3H7)-C6H4 H
1757 CH3 4-O-(i-C3H7)-C6H4 CH3
1758 CH3 4-O-(i-C3H7)-C6H4 C2H5
1759 CH3 4-O-(i-C3H7)-C6H4 n-C3H7
1760 CH3 4-O-(i-C3H7)-C6H4 i-C3H7
1761 CH3 4-O-(i-C3H7)-C6H4 n-C4H9
1762 CH3 4-O-(i-C3H7)-C6H4 t-C4H9
1763 CH3 4-O-(i-C3H7)-C6H4 n-C6H13
1764 CH3 4-O-(i-C3H7)-C6H4 Prop-1-en-3-yl
1765 CH3 4-O-(i-C3H7)-C6H4 (E) -1-chloroprop-1-en-3-yl
1766 CH3 4-O-(i-C3H7)-C6H4 Propin-3-yl
No. R3 R4 R5
1767 CH3 4-O-(i-C3H7)-C6H4 3-methyl-but-2-en-1-yl
1768 CH3 2-O-(t-C4H9)-C6H4 H
1769 CH3 2-O-(t-C4H9)-C6H4 CH3
1770 CH3 2-O-(t-C4H9)-C6H4 C2H5
1771 CH3 2-O-(t-C4H9)-C6H4 n-C3H7
1772 CH3 2-O-(t-C4H9)-C6H4 i-C3H7
1773 CH3 2-O-(t-C4H9)-C6H4 n-C4H9
1774 CH3 2-O-(t-C4H9)-C6H4 t-C4H9
1775 CH3 2-O-(t-C4H9)-C6H4 n-C6H13
1776 CH3 2-O-(t-C4H9)-C6H4 Prop-1-en-3-yl
1777 CH3 2-O-(t-C4H9)-C6H4 (E) -1-chloroprop-1-en-3-yl
1778 CH3 2-O-(t-C4H9)-C6H4 Propin-3-yl
1779 CH3 2-O-(t-C4H9)-C6H4 3-methyl-but-2-en-1-yl
1780 CH3 3-O-(t-C4H9)-C6H4 H
1781 CH3 3-O-(t-C4H9)-C6H4 CH3
1782 CH3 3-O-(t-C4H9)-C6H4 C2H5
1783 CH3 3-O-(t-C4H9)-C6H4 n-C3H7
1784 CH3 3-O-(t-C4H9)-C6H4 i-C3H7
1785 CH3 3-O-(t-C4H9)-C6H4 n-C4H9
1786 CH3 3-O-(t-C4H9)-C6H4 t-C4H9
1787 CH3 3-O-(t-C4H9)-C6H4 n-C6H13
1788 CH3 3-O-(t-C4H9)-C6H4 Prop-1-en-3-yl
1789 CH3 3-O-(t-C4H9)-C6H4 (E) -1-chloroprop-1-en-3-yl
1790 CH3 3-O-(t-C4H9)-C6H4 Propine-3-Base of
1791 CH3 3-O-(t-C4H9)-C6H4 3-methyl-but-2-en-1-yl
1792 CH3 4-O-(t-C4H9)-C6H4 H
1793 CH3 4-O-(t-C4H9)-C6H4 CH3
1794 CH3 4-O-(t-C4H9)-C6H4 C2H5
1795 CH3 4-O-(t-C4H9)-C6H4 n-C3H7
1796 CH3 4-O-(t-C4H9)-C6H4 i-C3H7
1797 CH3 4-O-(t-C4H9)-C6H4 n-C4H9
1798 CH3 4-O-(t-C4H9)-C6H4 t-C4H9
1799 CH3 4-O-(t-C4H9)-C6H4 n-C6H13
1800 CH3 4-O-(t-C4H9)-C6H4 Prop-1-en-3-yl
1801 CH3 4-O-(t-C4H9)-C6H4 (E) -1-chloroprop-1-en-3-yl
1802 CH3 4-O-(t-C4H9)-C6H4 Propin-3-yl
1803 CH3 4-O-(t-C4H9)-C6H4 3-methyl-but-2-en-1-yl
1804 CH3 2-CF3-C6H4 H
No. R3 R4 R5
1805 CH3 2-CF3-C6H4 CH3
1806 CH3 2-CF3-C6H4 C2H5
1807 CH3 2-CF3-C6H4 n-C3H7
1808 CH3 2-CF3-C6H4 i-C3H7
1809 CH3 2-CF3-C6H4 n-C4H9
1810 CH3 2-CF3-C6H4 t-C4H9
1811 CH3 2-CF3-C6H4 n-C6H13
1812 CH3 2-CF3-C6H4 Prop-1-en-3-yl
1813 CH3 2-CF3-C6H4 (E) -1-chloroprop-1-en-3-yl
1814 CH3 2-CF3-C6H4 Propin-3-yl
1815 CH3 2-CF3-C6H4 3-methyl-but-2-en-1-yl
1816 CH3 3-CF3-C6H4 H
1817 CH3 3-CF3-C6H4 CH3
1818 CH3 3-CF3-C6H4 C2H5
1819 CH3 3-CF3-C6H4 n-C3H7
1820 CH3 3-CF3-C6H4 i-C3H7
1821 CH3 3-CF3-C6H4 n-C4H9
1822 CH3 3-CF3-C6H4 t-C4H9
1823 CH3 3-CF3-C6H4 n-C6H13
1824 CH3 3-CF3-C6H4 Prop-1-en-3-yl
1825 CH3 3-CF3-C6H4 (E) -1-chloroprop-1-en-3-yl
1826 CH3 3-CF3-C6H4 Propin-3-yl
1827 CH3 3-CF3-C6H4 3-methyl-but-2-en-1-yl
1828 CH3 4-CF3-C6H4 H
1829 CH3 4-CF3-C6H4 CH3
1830 CH3 4-CF3-C6H4 C2H5
1831 CH3 4-CF3-C6H4 n-C3H7
1832 CH3 4-CF3-C6H4 i-C3H7
1833 CH3 4-CF3-C6H4 n-C4H9
1834 CH3 4-CF3-C6H4 t-C4H9
1835 CH3 4-CF3-C6H4 n-C6H13
1836 CH3 4-CF3-C6H4 Prop-1-en-3-yl
1837 CH3 4-CF3-C6H4 (E) -1-chloroprop-1-en-3-yl
1838 CH3 4-CF3-C6H4 Propin-3-yl
1839 CH3 4-CF3-C6H4 3-methyl-but-2-en-1-yl
1840 CH3 2-NH2-C6H4 H
1841 CH3 2-NH2-C6H4 CH3
1842 CH3 2-NH2-C6H4 C2H5
No. R3 R4 R5
1843 CH3 2-NH2-C6H4 n-C3H7
1844 CH3 2-NH2-C6H4 i-C3H7
1845 CH3 2-NH2-C6H4 n-C4H9
1846 CH3 2-NH2-C6H4 t-C4H9
1847 CH3 2-NH2-C6H4 n-C6H13
1848 CH3 2-NH2-C6H4 Prop-1-en-3-yl
1849 CH3 2-NH2-C6H4 (E) -1-chloroprop-1-en-3-yl
1850 CH3 2-NH2-C6H4 Propin-3-yl
1851 CH3 2-NH2-C6H4 3-methyl-but-2-en-1-yl
1852 CH3 3-NH2-C6H4 H
1853 CH3 3-NH2-C6H4 CH3
1854 CH3 3-NH2-C6H4 C2H5
1855 CH3 3-NH2-C6H4 n-C3H7
1856 CH3 3-NH2-C6H4 i-C3H7
1857 CH3 3-NH2-C6H4 n-C4H9
1858 CH3 3-NH2-C6H4 t-C4H9
1859 CH3 3-NH2-C6H4 n-C6H13
1860 CH3 3-NH2-C6H4 Prop-1-en-3-yl
1861 CH3 3-NH2-C6H4 (E) -1-chloroprop-1-en-3-yl
1862 CH3 3-NH2-C6H4 Propin-3-yl
1863 CH3 3-NH2-C6H4 3-methyl-but-2-en-1-yl
1864 CH3 4-NH2-C6H4 H
1865 CH3 4-NH2-C6H4 CH3
1866 CH3 4-NH2-C6H4 C2H5
1867 CH3 4-NH2-C6H4 n-C3H7
1868 CH3 4-NH2-C6H4 i-C3H7
1869 CH3 4-NH2-C6H4 n-C4H9
1870 CH3 4-NH2-C6H4 t-C4H9
1871 CH3 4-NH2-C6H4 n-C6H13
1872 CH3 4-NH2-C6H4 Prop-1-en-3-yl
1873 CH3 4-NH2-C6H4 (E) -1-chloroprop-1-en-3-yl
1874 CH3 4-NH2-C6H4 Propin-3-yl
1875 CH3 4-NH2-C6H4 3-methyl-but-2-en-1-yl
1876 CH3 2-NMe2-C6H4 H
1877 CH3 2-NMe2-C6H4 CH3
1878 CH3 2-NMe2-C6H4 C2H5
1879 CH3 2-NMe2-C6H4 n-C3H7
1880 CH3 2-NMe2-C6H4 i-C3H7
No. R3 R4 R5
1881 CH3 2-NMe2-C6H4 n-C4H9
1882 CH3 2-NMe2-C6H4 t-C4H9
1883 CH3 2-NMe2-C6H4 n-C6H13
1884 CH3 2-NMe2-C6H4 Prop-1-en-3-yl
1885 CH3 2-NMe2-C6H4 (E) -1-chloroprop-1-en-3-yl
1886 CH3 2-NMe2-C6H4 Propin-3-yl
1887 CH3 2-NMe2-C6H4 3-methyl-but-2-en-1-yl
1888 CH3 3-NMe2-C6H4 H
1889 CH3 3-NMe2-C6H4 CH3
1890 CH3 3-NMe2-C6H4 C2H5
1891 CH3 3-NMe2-C6H4 n-C3H7
1892 CH3 3-NMe2-C6H4 i-C3H7
1893 CH3 3-NMe2-C6H4 n-C4H9
1894 CH3 3-NMe2-C6H4 t-C4H9
1895 CH3 3-NMe2-C6H4 n-C6H13
1896 CH3 3-NMe2-C6H4 Prop-1-en-3-yl
1897 CH3 3-NMe2-C6H4 (E) -1-chloroprop-1-en-3-yl
1898 CH3 3-NMe2-C6H4 Propin-3-yl
1899 CH3 3-NMe2-C6H4 3-methyl-but-2-en-1-yl
1900 CH3 4-NMe2-C6H4 H
1901 CH3 4-NMe2-C6H4 CH3
1902 CH3 4-NMe2-C6H4 C2H5
1903 CH3 4-NMe2-C6H4 n-C3H7
1904 CH3 4-NMe2-C6H4 i-C3H7
1905 CH3 4-NMe2-C6H4 n-C4H9
1906 CH3 4-NMe2-C6H4 t-C4H9
1907 CH3 4-NMe2-C6H4 n-C6H13
1908 CH3 4-NMe2-C6H4 Prop-1-en-3-yl
1909 CH3 4-NMe2-C6H4 (E) -1-chloroprop-1-en-3-yl
1910 CH3 4-NMe2-C6H4 Propin-3-yl
1911 CH3 4-NMe2-C6H4 3-methyl-but-2-en-1-yl
1912 CH3 2-aminothiocarbonyl radical radical-C6H4 H
1913 CH3 2-aminothiocarbonyl radical radical-C6H4 CH3
1914 CH3 2-aminothiocarbonyl radical radical-C6H4 C2H5
1915 CH3 2-aminothiocarbonyl radical radical-C6H4 n-C3H7
No. R3 R4 R5
1916 CH3 2-aminothiocarbonyl radical -C6H4 i-C3H7
1917 CH3 2-aminothiocarbonyl radical -C6H4 n-C4H9
1918 CH3 2-aminothiocarbonyl radical -C6H4 t-C4H9
1919 CH3 2-Am aminothiocarbonyl -C6H4 n-C6H13
1920 CH3 2-Am aminothiocarbonyl -C6H4 Prop-1-en-3-yl
1921 CH3 2-Am aminothiocarbonyl -C6H4 (E) -1-chloroprop-1-en-3-yl
1922 CH3 2-aminothiocarbonyl radical -C6H4 Propin-3-yl
1923 CH3 2-A aminothiocarbonyl -C6H4 3-methyl-but-2-en-1-yl
1924 CH3 3-A aminothiocarbonyl -C6H4 H
1925 CH3 3-A aminothiocarbonyl -C6H4 CH3
1926 CH3 3-aminothiocarbonyl radical -C6H4 C2H5
1927 CH3 3-A aminothiocarbonyl -C6H4 n-C3H7
1928 CH3 3-A aminothiocarbonyl -C6H4 i-C3H7
1929 CH3 3-aminothiocarbonyl radical -C6H4 n-C4H9
1930 CH3 3-aminothiocarbonyl radical -C6H4 t-C4H9
1931 CH3 3-aminothiocarbonyl radical -C6H4 n-C6H13
1932 CH3 3-aminothiocarbonyl radical -C6H4 Prop-1-en-3-yl
1933 CH3 3-aminothiocarbonyl radical -C6H4 (E) -1-chloroprop-1-en-3-yl
1934 CH3 3-aminothiocarbonyl radical -C6H4 Propin-3-yl
1935 CH3 3-aminothiocarbonyl radical -C6H4 3-methyl-but-2-en-1-yl
1936 CH3 4-aminothiocarbonyl radical -C6H4 H
1937 CH3 4-aminothiocarbonyl radical -C6H4 CH3
1938 CH3 4-aminothiocarbonyl radical -C6H4 C2H5
No. R3 R4 R5
1939 CH3 4-aminothiocarbonyl radical -C6H4 n-C3H7
1940 CH3 4-aminothiocarbonyl radical -C6H4 i-C3H7
1941 CH3 4-aminothiocarbonyl radical -C6H4 n-C4H9
1942 CH3 4-aminothiocarbonyl radical -C6H4 t-C4H9
1943 CH3 4-aminothiocarbonyl radical -C6H4 n-C6H13
1944 CH3 4-aminothiocarbonyl radical -C6H4 C3-1-en-3-yl
1945 CH3 4-aminothiocarbonyl radical -C6H4 (E) -1-chloroprop-1-en-3-yl
1946 CH3 4-aminothiocarbonyl-C6H4 Propin-3-yl
1947 CH3 4-aminothiocarbonyl radical -C6H4 3-methyl-but-2-en-1-yl
1948 CH3 2-OCF3-C6H4 H
1949 CH3 2-OCF3-C6H4 CH3
1950 CH3 2-OCF3-C6H4 C2H5
1951 CH3 2-OCF3-C6H4 n-C3H7
1952 CH3 2-OCF3-C6H4 i-C3H7
1953 CH3 2-OCF3-C6H4 n-C4H9
1954 CH3 2-OCF3-C6H4 t-C4H9
1955 CH3 2-OCF3-C6H4 n-C6H13
1956 CH3 2-OCF3-C6H4 Prop-1-en-3-yl
1957 CH3 2-OCF3-C6H4 (E) -1-chloroprop-1-en-3-yl
1958 CH3 2-OCF3-C6H4 Propin-3-yl
1959 CH3 2-OCF3-C6H4 3-methyl-but-2-en-1-yl
1960 CH3 3-OCF3-C6H4 H
1961 CH3 3-OCF3-C6H4 CH3
1962 CH3 3-OCF3-C6H4 C2H5
1963 CH3 3-OCF3-C6H4 n-C3H7
1964 CH3 3-OCF3-C6H4 i-C3H7
1965 CH3 3-OCF3-C6H4 n-C4H9
1966 CH3 3-OCF3-C6H4 t-C4H9
1967 CH3 3-OCF3-C6H4 n-C6H13
1968 CH3 3-OCF3-C6H4 Prop-1-en-3-yl
1969 CH3 3-OCF3-C6H4 (E) -1-chloroprop-1-en-3-yl
1970 CH3 3-OCF3-C6H4 Propin-3-yl
No. R3 R4 R5
1971 CH3 3-OCF3-C6H4 3-methyl-but-2-en-1-yl
1972 CH3 4-OCF3-C6H4 H
1973 CH3 4-OCF3-C6H4 CH3
1974 CH3 4-OCF3-C6H4 C2H5
1975 CH3 4-OCF3-C6H4 n-C3H7
1976 CH3 4-OCF3-C6H4 i-C3H7
1977 CH3 4-OCF3-C6H4 n-C4H9
1978 CH3 4-OCF3-C6H4 t-C4H9
1979 CH3 4-OCF3-C6H4 n-C6H13
1980 CH3 4-OCF3-C6H4 Prop-1-en-3-yl
1981 CH3 4-OCF3-C6H4 (E) -1-chloroprop-1-en-3-yl
1982 CH3 4-OCF3-C6H4 Propin-3-yl
1983 CH3 4-OCF3-C6H4 3-methyl-but-2-en-1-yl
1984 CH3 2-SCH3-C6H4 H
1985 CH3 2-SCH3-C6H4 CH3
1986 CH3 2-SCH3-C6H4 C2H5
1987 CH3 2-SCH3-C6H4 n-C3H7
1988 CH3 2-SCH3-C6H4 i-C3H7
1989 CH3 2-SCH3-C6H4 n-C4H9
1990 CH3 2-SCH3-C6H4 t-C4H9
1991 CH3 2-SCH3-C6H4 n-C6H13
1992 CH3 2-SCH3-C6H4 Prop-1-en-3-yl
1993 CH3 2-SCH3-C6H4 (E) -1-chloroprop-1-en-3-yl
1994 CH3 2-SCH3-C6H4 Propin-3-yl
1995 CH3 2-SCH3-C6H4 3-methyl-but-2-en-1-yl
1996 CH3 3-SCH3-C6H4 H
1997 CH3 3-SCH3-C6H4 CH3
1998 CH3 3-SCH3-C6H4 C2H5
1999 CH3 3-SCH3-C6H4 n-C3H7
2000 CH3 3-SCH3-C6H4 i-C3H7
2001 CH3 3-SCH3-C6H4 n-C4H9
2002 CH3 3-SCH3-C6H4 t-C4H9
2003 CH3 3-SCH3-C6H4 n-C6H13
2004 CH3 3-SCH3-C6H4 Prop-1-en-3-yl
2005 CH3 3-SCH3-C6H4 (E) -1-chloroprop-1-en-3-yl
2006 CH3 3-SCH3-C6H4 Propin-3-yl
2007 CH3 3-SCH3-C6H4 3-methyl-but-2-en-1-yl
2008 CH3 4-SCH3-C6H4 H
No. R3 R4 R5
2009 CH3 4-SCH3-C6H4 CH3
2010 CH3 4-SCH3-C6H4 C2H5
2011 CH3 4-SCH3-C6H4 n-C3H7
2012 CH3 4-SCH3-C6H4 i-C3H7
2013 CH3 4-SCH3-C6H4 n-C4H9
2014 CH3 4-SCH3-C6H4 t-C4H9
2015 CH3 4-SCH3-C6H4 n-C6H13
2016 CH3 4-SCH3-C6H4 Prop-1-en-3-yl
2017 CH3 4-SCH3-C6H4 (E) -1-chloroprop-1-en-3-yl
2018 CH3 4-SCH3-C6H4 Propin-3-yl
2019 CH3 4-SCH3-C6H4 3-methyl-but-2-en-1-yl
2020 CH3 2-methanesulfonyl-C6H4 H
2021 CH3 2-methanesulfonyl-C6H4 CH3
2022 CH3 2-methanesulfonyl-C6H4 C2H5
2023 CH3 2-methanesulfonyl-C6H4 n-C3H7
2024 CH3 2-methanesulfonyl-C6H4 i-C3H7
2025 CH3 2-methanesulfonyl-C6H4 n-C4H9
2026 CH3 2-methanesulfonyl-C6H4 t-C4H9
2027 CH3 2-methanesulfonyl-C6H4 n-C6H13
2028 CH3 2-methanesulfonyl-C6H4 Prop-1-en-3-yl
2029 CH3 2-methanesulfonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2030 CH3 2-methanesulfonyl-C6H4 Propin-3-yl
2031 CH3 2-methanesulfonyl-C6H4 3-methyl-but-2-en-1-yl
2032 CH3 3-methanesulfonyl-C6H4 H
2033 CH3 3-methanesulfonyl-C6H4 CH3
2034 CH3 3-methanesulfonyl-C6H4 C2H5
2035 CH3 3-methanesulfonyl-C6H4 n-C3H7
No. R3 R4 R5
2036 CH3 3-methanesulfonyl-C6H4 i-C3H7
2037 CH3 3-methanesulfonyl-C6H4 n-C4H9
2038 CH3 3-methanesulfonyl-C6H4 t-C4H9
2039 CH3 3-methanesulfonyl-C6H4 n-C6H13
2040 CH3 3-methanesulfonyl-C6H4 Prop-1-en-3-yl
2041 CH3 3-methanesulfonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2042 CH3 3-methanesulfonyl-C6H4 Propin-3-yl
2043 CH3 3-methanesulfonyl-C6H4 3-methyl-but-2-en-1-yl
2044 CH3 4-Methanesulfonyl-C6H4 H
2045 CH3 4-Methanesulfonyl-C6H4 CH3
2046 CH3 4-Methanesulfonyl-C6H4 C2H5
2047 CH3 4-Methanesulfonyl-C6H4 n-C3H7
2048 CH3 4-Methanesulfonyl-C6H4 i-C3H7
2049 CH3 4-Methanesulfonyl-C6H4 n-C4H9
2050 CH3 4-Methanesulfonyl-C6H4 t-C4H9
2051 CH3 4-Methanesulfonyl-C6H4 n-C6H13
2052 CH3 4-Methanesulfonyl-C6H4 Prop-1-en-3-yl
2053 CH3 4-Methanesulfonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2054 CH3 4-Methanesulfonyl-C6H4 Propin-3-yl
2055 CH3 4-Methanesulfonyl-C6H4 3-methyl-but-2-en-1-yl
2056 CH3 2-methoxycarbonyl-C6H4 H
2057 CH3 2-methoxycarbonyl-C6H4 CH3
2058 CH3 2-methoxycarbonyl-C6H4 C2H5
No. R3 R4 R5
2059 CH3 2-methoxycarbonyl-C6H4 n-C3H7
2060 CH3 2-methoxycarbonyl-C6H4 i-C3H7
2061 CH3 2-methoxycarbonyl-C6H4 n-C4H9
2062 CH3 2-methoxycarbonyl-C6H4 t-C4H9
2063 CH3 2-methoxycarbonyl-C6H4 n-C6H13
2064 CH3 2-methoxycarbonyl-C6H4 Prop-1-en-3-yl
2065 CH3 2-methoxycarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2066 CH3 2-methoxycarbonyl-C6H4 Propin-3-yl
2067 CH3 2-methoxycarbonyl-C6H4 3-methyl-but-2-en-1-yl
2068 CH3 3-methoxycarbonyl-C6H4 H
2069 CH3 3-methoxycarbonyl-C6H4 CH3
2070 CH3 3-methoxycarbonyl-C6H4 C2H5
2071 CH3 3-methoxycarbonyl-C6H4 n-C3H7
2072 CH3 3-methoxycarbonyl-C6H4 i-C3H7
2073 CH3 3-methoxycarbonyl-C6H4 n-C4H9
2074 CH3 3-methoxycarbonyl-C6H4 t-C4H9
2075 CH3 3-methoxycarbonyl-C6H4 n-C6H13
2076 CH3 3-methoxycarbonyl-C6H4 Prop-1-en-3-yl
2077 CH3 3-methoxycarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2078 CH3 3-methoxycarbonyl-C6H4 Propin-3-yl
2079 CH3 3-methoxycarbonyl-C6H4 3-methyl-but-2-en-1-yl
2080 CH3 4-methoxycarbonyl-C6H4- H
2081 CH3 4-methoxycarbonyl-C6H4 CH3
No. R3 R4 R5
2082 CH3 4-methoxycarbonyl-C6H4 C2H5
2083 CH3 4-methoxycarbonyl-C6H4 n-C3H7
2084 CH3 4-methoxycarbonyl-C6H4 i-C3H7
2085 CH3 4-methoxycarbonyl-C6H4 n-C4H9
2086 CH3 4-methoxycarbonyl-C6H4 t-C4H9
2087 CH3 4-methoxycarbonyl-C6H4 n-C6H13
2088 CH3 4-methoxycarbonyl-C6H4 Prop-1-en-3-yl
2089 CH3 4-methoxycarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2090 CH3 4-methoxycarbonyl-C6H4 Propin-3-yl
2091 CH3 4-methoxycarbonyl-C6H4 3-methyl-but-2-en-1-yl
2092 CH3 2-ethoxycarbonyl-C6H4 H
2093 CH3 2-ethoxycarbonyl-C6H4 CH3
2094 CH3 2-ethoxycarbonyl-C6H4 C2H5
2095 CH3 2-ethoxycarbonyl-C6H4 n-C3H7
2096 CH3 2-ethoxycarbonyl-C6H4 i-C3H7
2097 CH3 2-ethoxycarbonyl-C6H4 n-C4H9
2098 CH3 2-ethoxycarbonyl-C6H4 t-C4H9
2099 CH3 2-ethoxycarbonyl-C6H4 n-C6H13
2100 CH3 2-ethoxycarbonyl-C6H4 Prop-1-en-3-yl
2101 CH3 2-ethoxycarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2102 CH3 2-ethoxycarbonyl-C6H4 Propin-3-yl
2103 CH3 2-ethoxycarbonyl-C6H4 3-methyl-but-2-en-1-yl
2104 CH3 3-ethoxycarbonyl-C6H4 H
No. R3 R4 R5
2105 CH3 3-ethoxycarbonyl-C6H4 CH3
2106 CH3 3-ethoxycarbonyl-C6H4 C2H5
2107 CH3 3-ethoxycarbonyl-C6H4 n-C3H7
2108 CH3 3-ethoxycarbonyl-C6H4 i-C3H7
2109 CH3 3-ethoxycarbonyl-C6H4 n-C4H9
2110 CH3 3-ethoxycarbonyl-C6H4 t-C4H9
2111 CH3 3-ethoxycarbonyl-C6H4 n-C6H13
2112 CH3 3-ethoxycarbonyl-C6H4 Prop-1-en-3-yl
2113 CH3 3-ethoxycarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2114 CH3 3-ethoxycarbonyl-C6H4 Propin-3-yl
2115 CH3 3-ethoxycarbonyl-C6H4 3-methyl-but-2-en-1-yl
2116 CH3 4-ethoxycarbonyl-C6H4 H
2117 CH3 4-ethoxycarbonyl-C6H4 CH3
2118 CH3 4-ethoxycarbonyl-C6H4 C2H5
2119 CH3 4-ethoxycarbonyl-C6H4 n-C3H7
2120 CH3 4-ethoxycarbonyl-C6H4 i-C3H7
2121 CH3 4-ethoxy groupCarbonyl group-C6H4 n-C4H9
2122 CH3 4-ethoxycarbonyl-C6H4 t-C4H9
2123 CH3 4-ethoxycarbonyl-C6H4 n-C6H13
2124 CH3 4-ethoxycarbonyl-C6H4 Prop-1-en-3-yl
2125 CH3 4-ethoxycarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2126 CH3 4-ethoxycarbonyl-C6H4 Propin-3-yl
2127 CH3 4-ethoxycarbonyl-C6H4 3-methyl-but-2-en-1-yl
No. R3 R4 R5
2128 CH3 2-aminocarbonyl-C6H4 H
2129 CH3 2-aminocarbonyl-C6H4 CH3
2130 CH3 2-aminocarbonyl-C6H4 C2H5
2131 CH3 2-aminocarbonyl-C6H4 n-C3H7
2132 CH3 2-aminocarbonyl-C6H4 i-C3H7
2133 CH3 2-aminocarbonyl-C6H4 n-C4H9
2134 CH3 2-aminocarbonyl-C6H4 t-C4H9
2135 CH3 2-aminocarbonyl-C6H4 n-C6H13
2136 CH3 2-aminocarbonyl-C6H4 Prop-1-en-3-yl
2137 CH3 2-aminocarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2138 CH3 2-aminocarbonyl-C6H4 Propin-3-yl
2139 CH3 2-aminocarbonyl-C6H4 3-methyl-but-2-en-1-yl
2140 CH3 3-aminocarbonyl-C6H4 H
2141 CH3 3-aminocarbonyl-C6H4 CH3
2142 CH3 3-aminocarbonyl-C6H4 C2H5
2143 CH3 3-aminocarbonyl-C6H4 n-C3H7
2144 CH3 3-aminocarbonyl-C6H4 i-C3H7
2145 CH3 3-aminocarbonyl-C6H4 n-C4H9
2146 CH3 3-aminocarbonyl-C6H4 t-C4H9
2147 CH3 3-aminocarbonyl-C6H4 n-C6H13
2148 CH3 3-aminocarbonyl-C6H4 Prop-1-en-3-yl
2149 CH3 3-aminocarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2150 CH3 3-aminocarbonyl-C6H4 Propin-3-yl
No. R3 R4 R5
2151 CH3 3-aminocarbonyl-C6H4 3-methyl-but-2-en-1-yl
2152 CH3 4-aminocarbonyl-C6H4 H
2153 CH3 4-aminocarbonyl-C6H4 CH3
2154 CH3 4-aminocarbonyl-C6H4 C2H5
2155 CH3 4-aminocarbonyl-C6H4 n-C3H7
2156 CH3 4-aminocarbonyl-C6H4 i-C3H7
2157 CH3 4-aminocarbonyl-C6H4 n-C4H9
2158 CH3 4-aminocarbonyl-C6H4 t-C4H9
2159 CH3 4-aminocarbonyl-C6H4 n-C6H13
2160 CH3 4-aminocarbonyl-C6H4 Prop-1-en-3-yl
2161 CH3 4-aminocarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2162 CH3 4-aminocarbonyl-C6H4 Propin-3-yl
2163 CH3 4-aminocarbonyl-C6H4 3-methyl-but-2-en-1-yl
2164 CH3 2- (N-methylaminocarbonyl) -C6H4 H
2165 CH3 2- (N-methylaminocarbonyl) -C6H4 CH3
2166 CH3 2- (N-methylaminocarbonyl) -C6H4 C2H5
2167 CH3 2- (N-methylaminocarbonyl) -C6H4 n-C3H7
2168 CH3 2- (N-methylaminocarbonyl) -C6H4 i-C3H7
2169 CH3 2- (N-methylaminocarbonyl) -C6H4 n-C4H9
2170 CH3 2- (N-methylaminocarbonyl) -C6H4 t-C4H9
2171 CH3 2- (N-methylaminocarbonyl) -C6H4 n-C6H13
2172 CH3 2- (N-methylaminocarbonyl) -C6H4 Prop-1-en-3-yl
2173 CH3 2- (N-methylaminocarbonyl) -C6H4 (E) -1-chloroprop-1-en-3-yl
No. R3 R4 R5
2174 CH3 2- (N-methylaminocarbonyl) -C6H4 Propin-3-yl
2175 CH3 2- (N-methylaminocarbonyl) -C6H4 3-methyl-but-2-en-1-yl
2176 CH3 3- (N-methylaminocarbonyl) -C6H4 H
2177 CH3 3- (N-methylaminocarbonyl) -C6H4 CH3
2178 CH3 3- (N-methylaminocarbonyl) -C6H4 C2H5
2179 CH3 3- (N-methylaminocarbonyl) -C6H4 n-C3H7
2180 CH3 3- (N-methylaminocarbonyl) -C6H4 i-C3H7
2181 CH3 3- (N-methylaminocarbonyl) -C6H4 n-C4H9
2182 CH3 3- (N-methylaminocarbonyl) -C6H4 t-C4H9
2183 CH3 3- (N-methylaminocarbonyl) -C6H4 n-C6H13
2184 CH3 3- (N-methylaminocarbonyl) -C6H4 Prop-1-en-3-yl
2185 CH3 3- (N-methylaminocarbonyl) -C6H4 (E) -1-chloroprop-1-en-3-yl
2186 CH3 3- (N-methylaminocarbonyl) -C6H4 Propin-3-yl
2187 CH3 3- (N-methylaminocarbonyl) -C6H4 3-methyl-but-2-en-1-yl
2188 CH3 4- (N-methylaminocarbonyl) -C6H4 H
2189 CH3 4- (N-methylaminocarbonyl) -C6H4 CH3
2190 CH3 4- (N-methylaminocarbonyl) -C6H4 C2H5
2191 CH3 4- (N-methylaminocarbonyl) -C6H4 n-C3H7
2192 CH3 4- (N-methylaminocarbonyl) -C6H4 i-C3H7
2193 CH3 4- (N-methylaminocarbonyl) -C6H4 n-C4H9
2194 CH3 4- (N-methylaminocarbonyl) -C6H4 t-C4H9
2195 CH3 4- (N-methylaminocarbonyl) -C6H4 n-C6H13
2196 CH3 4- (N-methylaminocarbonyl) -C6H4 Prop-1-en-3-yl
No. R3 R4 R5
2197 CH3 4- (N-methylaminocarbonyl) -C6H4 (E) -1-chloroprop-1-en-3-yl
2198 CH3 4- (N-methylaminocarbonyl) -C6H4 Propin-3-yl
2199 CH3 4- (N-methylaminocarbonyl) -C6H4 3-methyl-but-2-en-1-yl
2200 CH3 2-dimethylaminocarbonyl-C6H4 H
2201 CH3 2-dimethylaminocarbonyl-C6H4 CH3
2202 CH3 2-dimethylaminocarbonyl-C6H4 C2H5
2203 CH3 2-dimethylaminocarbonyl-C6H4 n-C3H7
2204 CH3 2-dimethylaminocarbonyl-C6H4 i-C3H7
2205 CH3 2-dimethylaminocarbonyl-C6H4 n-C4H9
2206 CH3 2-dimethylaminocarbonyl-C6H4 t-C4H9
2207 CH3 2-dimethylaminocarbonyl-C6H4 n-C6H13
2208 CH3 2-dimethylaminocarbonyl-C6H4 Prop-1-en-3-yl
2209 CH3 2-dimethylaminocarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2210 CH3 2-dimethylaminocarbonyl-C6H4 Propin-3-yl
2211 CH3 2-dimethylaminocarbonyl-C6H4 3-methyl-but-2-en-1-yl
2212 CH3 3-dimethylaminocarbonyl-C6H4 H
2213 CH3 3-dimethylaminocarbonyl-C6H4 CH3
2214 CH3 3-dimethylaminocarbonyl-C6H4 C2H5
2215 CH3 3-dimethylaminocarbonyl-C6H4 n-C3H7
2216 CH3 3-dimethylaminocarbonyl-C6H4 i-C3H7
2217 CH3 3-dimethylaminocarbonyl-C6H4 n-C4H9
2218 CH3 3-dimethylaminocarbonyl-C6H4 t-C4H9
2219 CH3 3-dimethylaminocarbonyl-C6H4 n-C6H13
No. R3 R4 R5
2220 CH3 3-dimethyl-ammoniaCarbonyl group-C6H4 Prop-1-en-3-yl
2221 CH3 3-dimethylaminocarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2222 CH3 3-dimethylaminocarbonyl-C6H4 Propin-3-yl
2223 CH3 3-dimethylaminocarbonyl-C6H4 3-methyl-but-2-en-1-yl
2224 CH3 4-dimethylaminocarbonyl-C6H4 H
2225 CH3 4-dimethylaminocarbonyl-C6H4 CH3
2226 CH3 4-dimethylaminocarbonyl-C6H4 C2H5
2227 CH3 4-dimethylaminocarbonyl-C6H4 n-C3H7
2228 CH3 4-dimethylaminocarbonyl-C6H4 i-C3H7
2229 CH3 4-dimethylaminocarbonyl-C6H4 n-C4H9
2230 CH3 4-dimethylaminocarbonyl-C6H4 t-C4H9
2231 CH3 4-dimethylaminocarbonyl-C6H4 n-C6H13
2232 CH3 4-dimethylaminocarbonyl-C6H4 Prop-1-en-3-yl
2233 CH3 4-dimethylaminocarbonyl-C6H4 (E) -1-chloroprop-1-en-3-yl
2234 CH3 4-dimethylaminocarbonyl-C6H4 Propin-3-yl
2235 CH3 4-dimethylaminocarbonyl-C6H4 3-methyl-but-2-en-1-yl
The compounds I are suitable as fungicides.
The compound I has very excellent broad-spectrum activity against plant pathogenic fungi, particularly pathogenic fungi of ascomycetes and basidiomycetes. They are in some cases systemically active and can be used as antifungal agents for leaves and soil.
They are of particular importance for controlling a wide variety of pathogenic fungi on various crops, such as wheat, rye, barley, oats, rice, maize, hemp, cotton, soya, coffee, sugar cane, grapes, fruit and ornamental and vegetable plants, such as cucumbers, beans, pumpkins, and on the seeds of these plants.
They are particularly suitable for controlling the following plant diseases: powdery mildew (powdery mildew) of cereals, powdery mildew and Sphaerotheca fuliginea of pumpkins, Podospora leucotrichum of apples, Leptosphaera leucotricha on grapevines, Podospora fungi of cereals, Rhizoctonia fungi of cotton and grasses, Ustilago fungi of cereals and sugarcanes, Venturia pomonella (scab) of apples, Helminthosporium species of cereals, Rhizoctonia cerealis of wheat, Staphylococcus gricola (gvedbad) of praecox, Castanea sativa
Figure A9519195901001
The cercospora herpotrichoides of Artemisia, wheat and barleyds, Pyricularia oryzae of rice, Phytophthora infestans of potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on grapevine, Alternaria species on vegetables and fruits.
The compounds I are used for combating fungi in plants, seeds or raw materials or for protecting soils from harmful fungi with active ingredients which achieve fungicidal efficacy. They are applied before or after fungal infection of the raw material, plant or seed.
They can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes or granules. The dosage form used depends on the application; but in any case a very fine and homogeneous dispersion in the cyclopropanecarboxylic acid ortho-substituted benzyl ester is ensured. The dosage forms are prepared in a manner known per se, for example by mixing the active compounds with solvents and/or with carriers, if desired emulsifiers or dispersants, it being possible for other organic solvents to be used as auxiliary solvents when water is used as diluent. Suitable auxiliary substances for this purpose include mainly: solvents such as aromatic compounds (e.g., diisopropyl isophthalate;
heterocyclic compounds, for example 2-heptadecyl-2-imidazolidine acetate, 2, 4-dichloro-6-10-chloroanilino-5-triazine, O, O-diethylbenzenedi (meth) imidophosphonothiosulphate, 5-amino-1- [ bis (dimethylamino) -phosphinyl]-3-phenyl-1, 2, 4-triazole, 2, 3-dicyano-1, 4-dithioanthraquinone, 2-thio-1, 3-dithiocyclopenta [ 4, 5-b]quinoxaline, methyl 1- (butylcarbamoyl) -2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2- (furan-2-yl) benzimidazole, 2- (thiazol-4-yl) benzimidazole, N- (1, 1, 2, 2-tetrachloroethylthio) tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide;
N-dichlorofluoromethylthio-N ', N' -dimethyl-N-phenylsulfonamide, 5-ethoxy-3-trichloromethyl-1, 2, 3-thiadiazole, 2-thiocyanomethylmethylthiobenzothiazole, 1, 4-dichloro-2, 5-dimethoxybenzene, 4- (2-chlorophenylhydrazononyl) -3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline or copper salt thereof, 2, 3-dihydro-5-carboxanilido-6-methyl-1, 4-oxathiiranyl hexadiene, 2, 3-dihydro-5-N-carboxanilido-6-methyl-1, 4-oxathiyl-4, 4-oxathiyl-2, 2-methyl-5, 6-dihydro-4H-pyran-3-N-formanilide, 2-methylfuran-3-N-formanilide, 2, 5-dimethylfuran-3-N-formanilide, 2, 4, 5-trimethylfuran-3-N-phenylcarbamoyl-2, N-chloro-2-ethyl-1, 2, 3-trichloromethyl-dichloro-thiobenzol-1, 6-methyl-1, 4-oxathi-1, 4-dichloro-1, 4-methyl-oxathi-2-1, 4-methyl-oxathi-2, 4-2-1, 4-oxathi-1, 4-2-oxathi-2-1, 4-or 2, 3-dichloro-5-2-1, 4-oxathi-2-1, 4-oxathi-2-1, 4-2-1, 2-dichloro-6-oxathi-1, 4-oxathi-6-oxathi-1, 2-1, 2-6-ethyl-methyl-oxathi-6-methyl-oxathi-2-6-methyl-1, 2-oxathi-1, 2-methyl-1, 2-1, 2-oxathi-1, 2-methyl-1, 2-1, 4-ethyl-1-methyl-2-1, 2-oxathi-ethyl-1, 2-1, 4-methyl-1, 4-oxathidiazirido-oxathidiazenidine, 2-1-methyl-1, 2-1-methyl-ethyl-1, 2-methyl-1, 4-methyl-1, 2-1-dichloro-methyl-1, 2-methyl-1, 2-1-methyl-1, 4-1-methyl-1, 2-methyl-1-dichloro-oxathidiazirido-methyl-1, 4-methyl-ethyl-methyl-1-ethyl-methyl-2-1-2-1, 2-1, 2-1-methyl-1-2-1, 2-1-2-6-1-2-6-2-ethyl-2-1, 4-1, 2-methyl-1, 2-dichloro-oxathidiazenidine, 2-ethyl-methyl-2-ethyl-2-ethyl-methyl-1, 2-1-methyl-1-6-ethyl-2-methyl-dichloro-methyl-2-methyl-dichloro-methyl-2-1, 6-2-1, 6-1, 4-methyl-1, 6-2-methyl-2-dichloro-methyl-2-methyl-2-dichloro-2-methyl-1, 6-2-1, 6-dichloro-2-dichloro-methyl-1-dichloro-2-.
The compounds of the formula I are also suitable for controlling insect, arachnid and nematode pests, and they can also be used as insecticides in plant protection and hygiene, in the protection of goods from storage and in veterinary medicine.
Harmful insects include butterflies (Lepidoptera), such as black cutworm, yellow cutworm, cotton leafworm, velvet looper, apple moth, oriental armyworm, looper, Cacoecia murrinana, carpura reterulana, winter caterpillar, spruce looper, western spruce looper, American armyworm, codling moth, European pine moth, cantaloupe moth, giant corn borer, Ehrlichia, ostrinia nubilalis, European corn borer, European pine needle biguella, European pine needle looper, Kochia scoparia, big wax moth, plum fruit borer, oriental fruit moth, cotton bollworm, American tobacco cutworm, American cotton bollworm, cabbage, Hiberniandefia, fall webworm, apple moth, tomato moth, Japanese beetle, beet, armyworm, coffee looper, coffee-spot looper, athetiopa moth, yellow cabbage looper, yellow cabbage moth, spodoptera exigua, pink bollworm, pinkeye, Autographa californica, tuber moth, leaf miner, cabbage caterpillar, fall armyworm, soybean looper, pine tip leaf moth, Scrobalpa absoluta, wheat moth, grape leaf roller, meadow armyworm, Spodoptera torlialis, prodenia litura, Thaumatopoa pitycocarpa, oak green leaf roller moth, cabbage looper, spruceleaf roller moth.
Beetles (coleoptera) such as rhidine, kowter beetle, tarnished beetle, jungle beetle, plum wood bark beetle, boll weevil, apple flower weevil, beet cryptophaga, pine bark beetle, Blitophaga undata, fava bean weevil, pisiform weevil, bruchus slirentis, apple leaf weevil, Cassidia nebulosa, bean leaf beetle, cabbage pod xylene, chlorinated aromatics (e.g., chlorobenzene), paraffins (e.g., petroleum fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide) and water; carrier materials such as minerals (e.g. kaolin, china clay, talc, chalk) and synthetic materials (e.g. highly dispersed silicic acid, silicates) in nature; emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates, and aryl sulfonates); and dispersants such as lignin-sulfite waste liquor and methyl cellulose.
The fungicidal compositions generally contain from 0.1 to 95%, preferably from 0.5 to 90%, by weight of active compound.
Depending on the type of action desired, from 0.01 to 2.0Kg of active compound per hectare are used.
In the treatment of seed, from 0.001 to 0.1g, preferably from 0.01 to 0.05g, of active compound per kg of seed are generally required.
The compositions of the invention may also be used as fungicides with other active substances, for example with herbicides, insecticides, growth regulators, bactericides or with fertilizers.
When mixed with other fungicides, the bactericidal range is increased in most cases.
The following are fungicides which can be used with the compounds of the invention, which are intended to illustrate the possibilities of combination, but are not limited to them:
sulfur, dithiocarbamates and their derivatives, such as iron dimethyldithiocarbamate, zinc ethylenebis-dithiocarbamate, manganese ethylenediamine bis-dithiocarbamate, tetramethylthiuram disulfide, zinc (N, N-ethylenebis-dithiocarbamate) ammine complex, zinc (N, N '-propylenedidithiocarbamic acid) complex, N' -polypropylenedibis (thiocarbamoyl) disulfide;
nitro derivatives, such as dinitro (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4, 6-dinitrophenyl 3, 3-dimethylacrylate, 2-sec-butyl-4, 6-dinitrophenyl isopropylcarbonate, 5-nitrobenzoate, Ceathorynchus napi, beet tibetan, tobacco wireworm, Asparagus cochinchinensis, longhorn leaf beetle, Diabrotica 12-punctata, corn rootworm, Mexican bean beetle, tobacco springtail weevil, cotton ash weevil, pine bark weevil, Egyptian alfalfa weevil, spruce bark beetle, Nicotiana baccatum, Nicotiana tabacum, Oryza uniflora, Melotha hippopastani, Pentaphyllum benthamoides, Trapa albus melolonha, rice rootworm, Orrrrynchus, Salicaria, Helicoccus, Phytophthora armorales hiensis, Phytophthora infestans, gomphrena, Tortoise, Tagetes insignis, Phyllotreta striolata, Japanese beetle, Pisum sativum leaf weevil, and Valeriana fauriei.
Diptera insects (ptera), such as Aedes aegypti, Aedes infestans, Citrus mexicana, Anopheles quinquefolius, Mediterranean fruit fly, Chrysomya perna, Chrysomya bominivora, Chrysomya camentomoides, Aedes perniciosa, Hematophaga, Culex pipiens, Culex cucurbitae, Oleanoplophora olea, Brassica podophylla, David Abies, Drosophila sericata, Parthenocidae, Haplodisia fortunei, seed fly, Erythrina dermatidae, Liriomyza sativae, Liriomyye a trifolii, Lucilia caprina [ sic], Lucilia cuprina, Lucilia sericata, Lycoriaria petralis, Triphytes operis, Musca domestica, Musca nasalis, Sweden wheat scaber, Phobia bigera, Physiosphaera, apple fly, Haemaria, and Haemaria taura.
Thrips (insects of the order Thysanoptera), such as tobacco brown thrips, alfalfa thrips, flower thrips, orange thrips, rice thrips, Frankliniella gromaculata, cotton thrips.
Membranous wing insects (hymenoptera) such as cabbage leaf bees, tropical leaf-cutting mosquitoes, texas japonica, leaf bees, apple leaf bees, chemeria cunea, fire ants, imported red fire ants.
Bed bugs (heteroptera), such as Lygus lucorum, cyrtopteris suturalensis, Lygus lucorum, dysedercus intermedius, eurygaster integriceps, lyfusus ignorum, Lygus phyllorum, Lygus pratensis, (Lygus lineolaris), Lygus pratensis, Lygus lucorum, lygadus pollicis, solubia neriis, lybenta perditor.
Insects (homoptera) that feed on plant juices, such as the aphids Lepidium meldonium, Aphidula nasutii, Aphidula nasturti, Aphis fabae, Aphis applianum, Aphisssambuci, Aphis cirsii, and Aphis brassicae; cerosipha gossypii, Dreyfusiaccordingly, Dreyfusia piceae, Dysaphis radicola, Dysaulacortina pseudostella, broad bean leafhopper, Myzus erysiphe, Myzus persicae, Myzodes persicae, Phosphaera virginiana, Piper graminis, Elephora delbrueckii, Physalis major, Pholiota oryzae, Phyllophora lactuca, Myxophysa, Phyllophora canephora, Phyllophora cerulosa, Psoralis virginosa, Psoralis palmata, Lipppahis mali, Myxophysalis maili, Aphis citri, Podosphaera citri, Trialeurophya viridis, Triales viridis, Trialeurophysa viridis, Pholiota viridis, Rhizopus vitis.
Termite (isoptera insects) such as Calotermes flaricollis, Leucotermes flaccipes, Reticulitermes lucifugas, Termestalensis.
Orthoptera insects (order orthoptera), such as cricket, periplaneta orientalis, blattaria germanica, auricularia, mole grasshopper in europe, locusta migratoria, grasshopper biglena, grasshopper red, grasshopper mexicana, grasshopper migratory grasshopper, grasshopper rocky mountain, locusta rubra, periplaneta americana, grasshopper americana, schistoserca peregrina, staronotus maroccanus greenhouse cricket .
Arachnidae, for example arachnidae (order Acarina), such as winter ticks, Cauliflower ticks, Cryptocaryon persicae, Ardisia circumcisalis, Boophilus discolor, Boophilus microplus, Brevibacterium purpureus, Carpentis lucorum, Dermacentor forest, Tetranychus horneri, Hedychium citriodorum, Hyalomma truncatum sheep hard tick, Rhipicephalus nervosa, Triptera infestans, Rhipicephalus aurifer, Tetranychus urticae, Tetranychus merdae, Dermatophagoides gallinae, Dermatophagoides pteronyssinus, Dermatophagoides pterus lateral, Dermanysfor, Rhipicephalus appendiculatus, Acarus scabiei, Tetranychus cinnabarinus, Tetranychus urticae, Tetranychus gossypii.
Nematodes, for example root-knot nematodes, such as Meloidogyne incognita, Meloidogyne cucumerini, Meloidogyne incognita, such as, Heliotrophila esculenta, Heterodera avenae, Heterodera glycines, Heterodera betanae, Heterodera trifoliata, nematodes of the stem and leaves, such as, Triplophytylodes longipes, Stellaria pilosa, Stenoloma elegans, Pleurotus elegans, Heterodera roborans, Pradenchus curvatus, Leptospira destructor.
The active compounds can be applied directly or in the form of their preparations, or else in the form of application preparations prepared therefrom, for example in the form of directly nebulizable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, powders, spreading compositions in the form of granules, by spraying, nebulizing, dusting, spreading or pouring, the form of application being completely determined by the intended use; in any case, the active compounds according to the invention should be as finely dispersed as possible.
The concentration of the active compound in the preparation intended for use may vary widely.
Generally, it is from 0.0001% to 10%, and more preferably in the range of 0.01% to 1%.
The active compounds have also achieved great success in the ultra low volume process (ULV), which makes it possible to use preparations with a weight proportion of 95% of active compound, even without additives to the active compound.
The active compounds are applied in an amount of 0.1 to 2.0, more preferably 0.2 to 1.0kg/ha for outdoor control of pests.
In the preparation of directly nebulizable solutions, emulsions, pastes or oil dispersions, suitable carriers are: mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, but also coal tar oils and oils from plants and animals, aliphatic, cyclic and aromatic compounds, such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
Aqueous dosage forms can be prepared by adding water to a concentrated emulsion, paste, or powder that can be mixed with water (oil dispersion). For the preparation of emulsions, pastes or oil dispersions, these substances can be mixed with water by means of moisturizers, viscosity-increasing agents, dispersants or emulsifiers to form a homogeneous substance or dissolved in oils or other solutions. However, it is also possible to prepare concentrates which comprise the active substance, a moisturizer, a tackifier, a dispersant or an emulsifier and possibly a solvent or an oil, and which are suitable for dilution with water.
Suitable surfactants are lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkali metal, alkaline earth metal and ammonium salts, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated aliphatic alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene phenolic ethers, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohol, isotridecyl alcohol, fatty alcohol ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin sulfite salinity liquid and methyl cellulose.
Powders, spreading compositions and dusts can be prepared by mixing or grinding the active compound with a solid carrier.
The formulations generally contain from 0.01 to 95%, more preferably from 0.1 to 90% by weight of active compound. The active compounds used here have a purity of from 90% to 100%, more preferably 95% to 100% (according to NMR spectrum).
Examples of formulations are:
i.5 parts by weight of active compound are mixed homogeneously with 95 parts by weight of finely divided kaolin. This gives a dust formulation containing 5% by weight of active substance.
II.30 parts by weight of active compound are mixed with 92 parts by weight of finely divided silica gel which has been sprayed with 8 parts by weight of paraffin oil on its surface. The process produces products with active substances having very good adhesion properties (23% by weight of active compound).
10 parts by weight of active compound are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of an adduct of 8 to 10mol of ethylene oxide to 1mol of oleic acid N-monoethanolamide, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of an adduct of 40mol of ethylene oxide to 1mol of castor oil (active compound content 9% by weight).
20 parts by weight of active compound are dissolved in a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of an adduct obtained by addition of 7mol of ethylene oxide to 1mol of isooctylphenol and 5 parts by weight of an adduct obtained by addition of 40mol of ethylene oxide to 1mol of castor oil (active compound content 16% by weight).
V. 80 parts by weight of the active compound are mixed with 3 parts by weight of sodium salt of diisobutylnaphthalene- α -sulphonic acid, 10 parts by weight of sodium lignosulphonate from the sulphite waste liquor and 7 parts by weight of pulverulent silica gel and the mixture is ground in a ball mill (active compound content 80% by weight).
90 parts by weight of active compound are mixed with 10 parts by weight of N-methyl- α -pyrrolidine to give a solution which is suitable for use in the form of fine droplets (active compound content 90% by weight).
20 parts by weight of active compound are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct obtained by addition of 7mol of ethylene oxide to 1mol of isooctylphenol and 10 parts by weight of the adduct obtained by addition of 40mol of ethylene oxide to 1mol of castor oil. This solution is poured and finely dispersed in 100000 parts by weight of water to give an aqueous dispersion which contains 0.02% by weight of active compound.
20 parts by weight of active compound are mixed with 3 parts by weight of sodium diisobutylnaphthalene- α -sulfonate, 17 parts by weight of the sodium salt of lignosulfonic acid obtained from sulfite waste liquor and 60 parts by weight of powdered silica gel, and the mixture is ground to a fine powder in a ball mill and finely dispersed in 20,000 parts by weight of water to give a spray containing 0.1% by weight of active compound.
Granules, such as coated, impregnated and homogeneous granules, can be prepared by binding the active compound on a solid carrier. Solid supports are, for example: mineral earths, such as silica gel, silicic acid, silica gel, silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide; pulverized synthetic materials, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; and vegetable products such as cereal flours, bark, wood or nut shell flours, cellulose flours; and other solid supports.
Various types of oils, herbicides, fungicides, other insecticides and bactericides can be added to the active compounds if appropriate only immediately before use (mixing in a container). These substances may be added to the compositions according to the invention in a weight ratio of from 1: 10 to 10: 1.
Synthesis examples:
the starting compounds were converted into compound I by suitable methods in the procedures described in the synthesis examples below, and the compounds thus obtained and their physical parameters are listed in the tables that follow.
Synthetic examples
Example 1
Preparation of methyl (E, E) -2-methoxyimino-2- [ 2' - (1 "-methyl, 1" -acetyl) iminooxymethyl]phenylacetate
21g (0.21mol) of diacetylmonoxime are added to 6.4g (0) in solution under protective gas conditions and with slight cooling at room temperature.21mol) sodium hydride(80%) in 150ml of anhydrous dimethylformamide and the mixture is stirred at room temperature for 30 minutes. Then, a solution of 60g (0.21mol) of methyl 2-methoxyimino-2- (2' -bromomethyl) phenylacetate dissolved in 360ml of dimethylformamide was added dropwise, and the mixture was stirred at room temperature for 16 hours. After addition of 10% strength hydrochloric acid, extraction was carried out with methyl tert-butyl ether. The combined organic phases were washed with water and Na2SO4Dried and concentrated. The residue is suspended in a small amount of cold methanol and, after suction filtration, 38g (59%) of the title compound are obtained as light brown crystals, m.p. 69-71 ℃.1H-NMR(CDCl3)：δ＝1.87(s，3H)；2.30(s，3H)；3.85(s，3H)；4.05(s，3H)；5.15(s，2H)；7.17-7.48(m，4H)ppm.
Example 2
Preparation of methyl (E, E, E-2-methoxyimino-2- [ 2' - (1 "-methyl, 1" - (1 "-ethoxyiminoethyl)) iminooxymethyl]phenylacetate
To a solution of methyl (E, E) -2-methoxyimino-2- [ 2' - (1 "-methyl, 1" -acetyl) iminooxymethyl]phenylacetate (2.5 g, 8.2mmol) in 60ml of hot methanol was added a solution of the above solution, which was cooled to room temperature, followed by addition of 0.96g of the above solution(9.8mmol) O-ethylhydroxylamine hydrochloride and 0.6g of molecular sieve particles (3A), and the mixture was left at room temperature for 5 days. After filtration off the molecular sieves, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, the organic phase is washed with water and Na2SO4Drying and concentration, trituration of the residue with n-hexane and suction filtration gave 1.8g (63%) of the title compound as pale yellow crystals with a melting point of 69-72 ℃.1H-NMR(CDCl3)：δ＝1.27(t，3H)；1.96(s，3H)；1.99(s，3H)；3.84(s，3H)；4.04(s，3H)；4.17(q，2H)；5.06(s，2H)；7.17-7.49(m，4H)ppm
Example 3
Preparation of S-methyl (E, E, E) -2-methoxyimino-2- [ 2' - (1 "-methyl, 1" - (1 "-ethoxyiminoethyl)) iminooxymethyl]phenylthioacetate.
7.0g (20mmol) of (E, E, E) -2-methoxyimino-2- [ 2' - (1 "-methyl, 1" - (1. sup. -ethoxyimino) are introducedEthyl)) methyl iminomethyl]phenylacetate was heated in 60ml of a 1MKOH aqueous solution at 80 ℃ for 4 hours. After cooling, the mixture is extracted with methyl tert-butyl ether, the aqueous phase is acidified with hydrochloric acid and extracted with methyl tert-butyl ether. The organic phase is washed with water and dried (Na)2SO4) And concentrated to give 6.0g of (E, E, E) -2-methoxyimino-2- [ 2' - (1 "-methyl, 1" - (1-ethoxyiminoethyl)) iminooxymethyl]phenylacetic acid as a white solid, which was dissolved in 100ml of anhydrous DMF. After addition of 2.9g (18mmol) of carbonyldiimidazole, the mixture is stirred for 1 hour, then 2.5g (36mmol) of sodium thiomethoxide are added and stirring is continued for 16 hours. The mixture was concentrated, the residue was taken up in methyl tert-butyl ether and water, the organic phase was extracted with 1M aqueous NaOH, washed with water and Na2SO4Dried and concentrated. 4.1g (57%) of the title compound are obtained as a pale yellow oil.1H-NMR(CDCl3)；δ＝1.27(t，3H)；1.95(s，3H)；1.98(s，3H)；2.33(s，3H)；4.05(s，3H)；4.17(q，2H)；5.03(s，2H)；7.12-7.48(m，4H)ppm.Table:
Figure A9519195901121
No. R2 m R3 R4 R5 Data
1 H CH3 CH3 CH3 Oil；IR(Film)：2935，1667， 1145，1057，1030，1014，988， 888，881，844，773
2 H CH3 CH3 C2H5 Oil；IR(Film)：2936，1679， 1386，1366，1091，1047，1027， 982，890，847
examples of the action against harmful fungi:
the fungicidal activity of the compounds of formula I can be demonstrated by the following experiments:
mixing the active compound with 70 wt% cyclohexanone and 20 wt% NekanilRLN(LutensolRAP6, moisturizing agent with emulsifying and dispersing activity, based on ethoxylated alkanesPhenyl phenol) and 10% by weight of EmulphorREL(EulanREL, emulsifier based on ethoxylated fatty alcohol) was prepared as a 20% strength emulsion and diluted with water to the desired corresponding strength.
1. Amycota graminicola (Erysiphe graminis Var.tritici)
Wheat seedlings (Kanzler variety) leaves were first treated with an aqueous preparation of the active compound (containing 63 ppm). After about 24 hours, the plants were sprinkled with wheat flour mold spores (Erysiphe graminis var. tritici). The plants thus treated were then cultivated for 7 days at 20-22 ℃ and 75-80% relative humidity. The extent of fungal growth was then determined.
In this test, the plants treated with the compounds according to the invention were infested, 40% of the plants treated with the known active compounds (EP-A463488, Table 2, No.497 compound) and 70% of the untreated plants.
Examples of Activity against animal pests
The insecticidal activity of the compounds of formula I can be shown by the following tests:
mixing the active compound
a) Prepared as a0.1% strength solution in acetone or
b) In 70% by weight cyclohexanol, 20% by weight NekanilRLN(LutensolRAP6, moisturizer with emulsifying and dispersing activity, based on ethoxylated alkylphenol) and 10% by weight of EmulphorREL (emulsifier based on ethoxylated fatty alcohol) mixtures were prepared as 10% strength emulsions and diluted accordingly with acetone in a) and water in b) to the desired concentration.
After the end of the test, the lowest concentration (action limit or lowest concentration) at which the test compound can still lead to an inhibition of 80 to 100% or mortality in each case in comparison with the untreated control is determined.

Claims (13)

1. Phenylacetic acid derivatives represented by the formula I and salts thereof
Wherein the substituents and symbols are as defined below:
R1is hydrogen or C1-C4-an alkyl group;
R2is cyano, nitro, trifluoromethyl, halogen, C1-C4-alkyl or C1
-C4-an alkoxy group;
m is 0, 1 or 2, R if m is 22Can be different groups;
R3is hydrogen, cyano, nitro, hydroxy, amino, halogen, C1-C4-an alkyl group,
C1-C4-haloalkyl radical, C1-C4-alkoxy radical, C1-C4-halo
Alkoxy radicals, C1-C4Alkylthio radical, C1-C4Alkylamino or bis-
C1-C4-analkylamino group;
R4is hydrogen, cyano, nitro, hydroxy, amino, halogen, C1-C6-an alkyl group,
C1-C6-alkoxy radical, C1-C6Alkylthio radical, C1-C6Alkyl ammonia
Base, bis-C1-C6-alkylamino radical, C2-C6-alkenyl radical, C2
-C6-alkenyloxy, C2-C6Alkenylthio radical, C2-C6-chain
Alkenylamino, N-C2-C6-alkenyl-N-C1-C6Alkyl ammonia
Base, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6
Alkylenethiol, C2-C6Alkynylamino, N-C2-C6-alkynes
radical-N-C1-C6Alkylamino, the hydrocarbon radicals in these radicals being part of
Partially or fully halogenated or carrying one to three of the following groups: cyano radicals, nitro radicals
Hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen
Element, C1-C6Alkylamino carbonyl, bis-C1-C6-alkylaminocarbonyl radicals
Base, C1-C6Alkylamino thiocarbonyl, bis-C1-C6Alkyl ammoniaThiocarbonyl radical, C1-C6-alkylsulfonyl, C1-C6Alkylsulfinyl radical, C1-C6-alkoxy radical, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6Alkylthio radical, C1-C6Alkylamino, bis-C1-C6-alkylamino radical, C2-C6Alkenoxy radical, C3-C6-cycloalkyl radical, C3-C6Cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-C4Alkoxy, arylthio, aryl-C1-C4Alkylthio, heteroaryl, heteroaryloxy, heteroaryl-C1-C4Alkoxy, heteroarylthio, heteroaryl-C1-C4Alkylthio, these cyclic groups being able in turn to be partially or completely halogenated in part and/or carrying one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6Alkyl radical, C1-C6-haloalkyl radical, C1-C6-alkylsulfonyl, C1-C6-alkylsulfinyl radical, C3-C6-cycloalkyl radical, C1-C6-alkoxy radical, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6Alkylthio radical, C1-C6Alkylamino, bis-C1-C6-alkanesAlkylamino radical, C1-C6Alkylamino carbonyl, bis-C1-C6-alkylaminocarbonyl radical, C1-C6Alkylamino thiocarbonyl, bis-C1-C6-alkylaminothiocarbonyl radical, C2-C6-alkenyl radical, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, and C (═ NOR)6)-An-R7；C3-C6-cycloalkyl radical, C3-C6Cycloalkoxy, C3-C6Cycloalkylthio radical, C3-C6Cycloalkylamino, N-C3-C6-cycloalkyl-N-C1-C6-alkylamino radical, C3-C6-cycloalkenyl radical, C3-C6-Cycloalkenyloxy, C3-C6-Cycloalkenylthio group, C3-C6Cycloalkenylamino, N-C3-C6-cycloalkenyl-N-C1-C6Alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-C1-C6Alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-C1-C6Alkylamino, heteroaryl, heteroaryloxy, heteroarylthio, heteroarylamino, N-heteroaryl-N-C1-
C6Alkylamino, the cyclic radical being partially or fully halogenated or carrying one to
Three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl,
aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl radical, C1-C6
-haloalkyl radical, C1-C6-alkylsulfonyl, C1-C6Alkyl ene
Sulfonyl radical, C3-C6-cycloalkyl radical, C1-C6-alkoxy radical, C1-
C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6Alkyl sulfide
Base, C1-C6Alkylamino, bis-C1-C6-alkylamino radical, C1
-C6Alkylamino carbonyl, bis-C1-C6-alkylaminocarbonyl radical, C1
-C6Alkylamino thiocarbonyl, bis-C1-C6-alkylaminothio
Carbonyl group, C2-C6-alkenyl radical, C2-C6-an alkenyloxy group, a benzyl group,
benzyloxy, aryl, aryloxy, heteroaryl and heteroaryloxy; r5Is a hydrogen atom, and is,
C1-C10-alkyl radical, C3-C6-cycloalkyl radical, C2-C10-alkenes
Base, C2-C10-alkynyl, C1-C10-alkylcarbonyl group, C2-C10
-alkenylcarbonyl radical, C3-C10Alkynylcarbonyl or C1-C10-alkyl sulfonic acid
Acyl radicals which may be partially or fully halogenated or carry one to three of the following
Group (b): cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl,
aminothiocarbonyl, halogen, C1-C6-alkyl radical, C1-C6-halo
Alkyl radical, C1-C6-alkylsulfonyl, C1-C6-alkylsulfinyl
Base, C1-C6-alkoxy radical, C1-C6-haloalkoxy, C1-
C6-alkoxycarbonyl, C1-C6Alkylthio radical, C1-C6-an alkylamino group,
bis-C1-C6-alkylamino radical, C1-C6Alkylamino carbonyl, bis-
C1-C6-alkylaminocarbonyl radical, C1-C6-an alkylamino-thiocarbonyl group,
bis-C1-C6-alkylaminothiocarbonyl radical, C2-C6-an alkenyl group,
C2-C6-alkenyloxy, C3-C6-cycloalkyl radical, C3-C6-Ring
Alkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy
Aryl, arylthio, heteroaryl, heteroaryloxy and heteroarylthio radicals, cyclic radicals
The radicals may in turn be partially or completely halogenated or carry one to three of the following groups: cyanogen (CN)
Radical, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothio
Carbonyl, halogen, C1-C6-alkyl radical, C1-C6-haloalkyl radical, C1
-C6-alkylsulfonyl, C1-C6-alkylsulfinyl radical, C3-C6
-cycloalkyl radical, C1-C6-alkoxy radical, C1-C6-a halogenated alkoxy group,
C1-C6-alkoxycarbonyl, C1-C6Alkylthio radical, C1-C6-alkanes
Amino, bis-C1-C6-alkylamino radical, C1-C6-an alkyl-amino-carbonyl group,
bis-C1-C6-alkylaminocarbonyl radical, C1-C6Alkylamino thiocarbonyls
Base, bis-C1-C6-alkylaminothiocarbonyl radical, C2-C6-alkenes
Base, C2-C6Alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,
arylthio, heteroaryl, heteroaryloxy, heteroarylthio, or
C(＝NOR6)-An-R7；
Aryl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylcarbonyl or hetaryl
Alkylsulfonyl radicals, which may be partially or fully halogenated or carry one to three
The following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, amino
Carbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl radical, C1-C6-
Haloalkyl, C1-C6-alkylcarbonyl group, C1-C6-alkylsulfonyl
Base, C1-C6-alkylsulfinyl radical, C3-C6-cycloalkyl radical, C1
-C6-alkoxy radical, C1-C6-haloalkoxy, C1-C6-alkoxy radical
Carbonyl group, C1-C6Alkylthio radical, C1-C6Alkylamino, bis-C1-
C6-alkylamino radical, C1-C6Alkylamino carbonyl, bis-C1-C6-
Alkylaminocarbonyl radical, C1-C6Alkylamino thiocarbonyl, bis-C1-
C6-alkylaminothiocarbonyl radical, C2-C6Alkenyl radical, C2-C6-chain
Alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy
Radical or C (═ NOR)6)-An-R7(ii) a Wherein A is oxygen, sulfur or nitrogen, wherein the nitrogen carries hydrogen or C1-C6An alkyl group; n is 0 or 1; r6Is hydrogen or C1-C6-alkyl, and R7Is hydrogen or C1-C6-an alkyl group.
2. A compound of formula I according to claim 1, wherein R is3、R4And R5The definition is as follows: r3Is hydrogen, hydroxy, cyclopropyl, halogen, C1-C4Alkyl radical, C1-C4
-alkoxy or C1-C4-alkylthio radical, R4Is hydrogen, hydroxy, halogen, cyclopropyl, cyclohexyl, C1-C4-an alkyl group,
C1-C4-alkoxy radical, C1-C4-an alkylthio group,
aryl or heteroaryl radicals which may be partially or fully halogenated or carry one to
Three groups selected from: cyano, nitro, hydroxy, mercapto, amino,
carboxy, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-an alkyl group,
C1-C6-haloalkyl radical, C1-C6-alkylsulfonyl, C1-C6
-alkylsulfinyl radical, C3-C6-cycloalkyl radical, C1-C6-an alkoxy group,
C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6
Alkylthio radical, C1-C6Alkylamino, bis-C1-C6-an alkylamino group,
C1-C6alkylamino carbonyl, bis-C1-C6Alkyl aminocarbonyl radical, C1
-C6Alkylamino thiocarbonyl, bis-C1-C6-alkylaminocarbonyl radicals
Base, C2-C6-alkenyl radical, C2-C6Alkenoxy, benzyl
Oxyaryl, aryloxy, heteroaryl and heteroaryloxy groups; r5Is a hydrogen atom, and is,
C1-C10-alkyl radical, C3-C6-cycloalkyl radical, C2-C10-alkenes
Base, C2-C10-alkynyl, C1-C10-alkylcarbonyl group, C2-C10
-alkenylcarbonyl radical, C3-C10Alkynylcarbonyl or C1-C10-alkylsulfonyl
These radicals may be partially or fully halogenated or carry one to three radicals selected from
The group of the following: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl
Radicals, aminothiocarbonyl, halogen, C1-C6-alkyl radical, C1-C6-
Haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkyl sulfin
Acyl radical, C3-C6-cycloalkyl radical, C1-C6-alkoxy radical, C1-C6
-haloalkyl radical, C1-C6-alkoxycarbonyl, C1-C6-an alkylthio group,
C1-C6alkylamino, bis-C1-C6-alkylamino radical, C1-C6
Alkyl aminocarbonyl, bis-C1-C6Alkyl aminocarbonyl radical, C1-C6-
Alkylamino thiocarbonyl, bis-C1-C6-alkylamino thiocarbonyl radical, C2
-C6-alkenyl radical, C2-C6Alkenoxy, benzyl, benzyloxy, aryl
Aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, which are useful as herbicides
Some of the aryl and heteroaryl radicals may in turn be partially or fully halogenated and/or bear one to three
The following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, amino
Carbonyl, aminothiocarbonyl, halogen,C1-C6-alkyl radical, C1-C6
-haloalkyl radical, C1-C6-alkylsulfonyl, C1-C6Alkyl ene
Sulfonyl radical, C3-C6-cycloalkyl radical, C1-C6-alkoxy radical, C1-C6
-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-an alkylthio group,
C1-C6alkylamino, bis-C1-C6-alkylamino radical, C1-C6-
Alkylamino carbonyl, bis-C1-C6Alkyl aminocarbonyl radical, C1-C6-alkanes
Aminothiocarbonyl, bis-C1-C6-alkylaminothiocarbonyl radical, C2-
C6-alkenyl radical, C2-C6Alkenoxy, benzyl, benzyloxy, aryl
Aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio or C
(＝NOR6)-An-R7；
Wherein
A is oxygen, sulfur or nitrogen, and the nitrogen carries hydrogen or C1-C6An alkyl group;
n is 0 or 1;
R6is hydrogen or C1-C6An alkyl group; and
R7is hydrogen or C1-C6An alkyl group.
3. Compounds of formula I according to claim 1, wherein m is 0.
4. A compound of formula I according to claim 1, wherein R1Is methyl.
5. Preparation of wherein R3A process for preparing compounds of formula I according to claim 1 which are not halogenIncluded are benzyl derivatives of the formula II, in a manner known per se.
Figure A9519195900071
Wherein L is1Is a leaving group which can be displaced nucleophilically,
with hydroxyimines of the formula III
R5ON＝C(R4)-C(R3)＝NOH III。
6. Preparation of wherein R3And R4A process for preparing compounds of the formula I as claimed in claim 1 which are not halogen, which comprises reacting a benzyl derivative of the formula II as claimed in claim 5 with a dihydroxyimine of the formula IV in a manner known per se
HON＝C(R4)-C(R3)＝NOH IV
Reacting to obtain the compound of formula V
Figure A9519195900081
And then reacting V with a compound of formula VI
R5-L2VI
Wherein L is2Being a leaving group which can be nucleophilically substituted
And reacting to obtain I.
7. Preparation of wherein R3A process for preparing compounds of the formula I as claimed in claim 1 which are not halogen, which comprises reacting benzyl derivatives of the formula II as claimed in claim 5 with carbonylhydroxyimines of the formula VIIa in a manner known per se
O＝C(R4)-C(R3)＝NOH VIIa
Reaction to give the compound of formula VIII
Figure A9519195900082
Then let VIII
a) First with hydroxylamine or a salt thereof and then with a compound of the formula VI (R) according to claim 65-L2) The compound is reacted, or
b) With hydroxylamine or hydroxylammonium salts of the formula IXa or IXb,
R5-ONH2R5-ONH3 _Q_
IXa Ixb
wherein Q_Is an acid radical ion
To obtain I.
8. A composition against animal pests or harmful fungi, which comprises customary additives and an effective amount of a compound of the formula I according to claim 1.
9. A method for controlling animal pests or harmful fungi, which comprises treating the pests or harmful fungi, their environment or the plants, surfaces, substances or spaces in which they live, with an effective amount of a compound of the formula I according to claim 1, in order to protect them from the pests and the harmful fungi.
10. The use of compounds I according to claim 1 for preparing compositions against animal pests and harmful fungi.
11. The use of compounds I according to claim 1 for animal pests and harmful fungi.
12. The compound of claim 7 of formula VIII.
13. Use of a compound of formula VIII according to claim 7 as an intermediate.
CN95191959.8A 1994-02-04 1995-01-03 Phenylthio acetic acid derivatives, process and intermediate products for their production and agents containing them Pending CN1143361A (en)

Applications Claiming Priority (4)

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DEP4403446.6 1994-02-04
DE4403446 1994-02-04
DE4421181 1994-06-17
DEP4421181.3 1994-06-17

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HUP9801635A3 (en) * 1995-04-08 2001-05-28 Basf Ag Method of preparing essentially pure isomers of alfa-bis-oximes
ATE374188T1 (en) * 1995-08-15 2007-10-15 Bayer Cropscience Ag PESTICIDES INDAZOLE DERIVATIVES
AR004012A1 (en) 1995-10-10 1998-09-30 Basf Ag DERIVATIVES OF PHENYLACETIC ACID, PROCEDURES FOR ITS OBTAINING, ITS USE TO PREPARE COMPOUNDS TO FIGHT ANIMALS OR HARMFUL FUNGI, THE COMPOSITIONS SO OBTAINED AND THE PROCEDURES FOR THE APPLICATION OF SUCH COMPOSITIONS.
WO1997016427A1 (en) * 1995-11-02 1997-05-09 Basf Aktiengesellschaft Pyridylacetic acid derivatives, process and intermediate products for their preparation, and their use
CZ173198A3 (en) * 1995-12-07 1998-08-12 Novartis Ag Process for preparing pesticides
BR9611811A (en) * 1995-12-07 1999-02-23 Novartis Ag Novartissa Novarti Pesticides
WO1997037968A1 (en) * 1996-04-11 1997-10-16 Shionogi & Co., Ltd. α-ALKOXYIMINOBENZYL DERIVATIVES AND AGRICULTURAL CHEMICALS CONTAINING THEM AS ACTIVE INGREDIENTS
CO5050364A1 (en) 1997-05-28 2001-06-27 Basf Ag METHOD TO CONTROL HARMFUL FUNGES
US6313344B1 (en) 1998-05-27 2001-11-06 Bayer Aktiengesellschaft Organic compounds

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ES2067570T3 (en) * 1988-12-29 1995-04-01 Ciba Geigy Ag METHYL ESTERS OF ALDIMINO- OR CETIMINO-OXI-ORTOTOLYL ACRYLIC ACIDS, OBTAINING THE SAME AND FUNGICIDES THAT CONTAIN THEM.
US5112860A (en) * 1989-11-16 1992-05-12 Basf Aktiengesellschaft Thiocarboxylic esters and fungicides containing them
US5187170A (en) * 1989-11-16 1993-02-16 Basf Aktiengesellschaft Thiocarboxylic esters and fungicides containing them
ATE161007T1 (en) * 1990-06-27 1997-12-15 Basf Ag O-BENZYL OXIMETHERS AND PLANT PROTECTION PRODUCTS CONTAINING THESE COMPOUNDS

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HUT76523A (en) 1997-09-29
AU1454795A (en) 1995-08-21
CZ231796A3 (en) 1997-02-12
AU686304B2 (en) 1998-02-05
BR9506718A (en) 1997-09-23
CA2182406A1 (en) 1995-08-10
WO1995021156A1 (en) 1995-08-10
MX9603175A (en) 1997-04-30
IL112480A0 (en) 1995-03-30
JPH09508396A (en) 1997-08-26
SK102296A3 (en) 1997-04-09
EP0741698A1 (en) 1996-11-13

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