TREA

Acrylates and fungicides containing them

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Information

  • Patent Grant
  • 5003101
  • Patent Number
    5,003,101
  • Date Filed
    Friday, May 5, 1989
    35 years ago
  • Date Issued
    Tuesday, March 26, 1991
    33 years ago
Information
Abstract
X is hydrogen, halogen, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted haloalkyl,n is 1, 2, 3 or 4,Y is substituted or unsubstituted alkylene, alkenylene, alkynylene, O, S(O), unsubstituted or alkyl-substituted N, oxycarbonyl, carbonyloxy, carbonyloxyalkylene, oxycarbonylalkylene, oxyalkylene, thioalkylene, azo, carbonylamino, aminocarbonyl, ##STR2## methylenoxy or methylenethio and Z is hydrogen, alkyl, cycloalkyl, aryl, aralkyl, aralkenyl, aralkoxy, aryloxy, aryloxyalkyl, hetaryl, alkoxy, alkoxyalkyl, alkylthio, or haloalkyl, these radicals being unsubstituted or substituted by halogen, cyano, nitro, alkyl, alkenyl, haloalkenyl, alkoxy, haloalkyl, alkoxycarbonyl or unsubstituted or substituted phenyl,and fungicides containing these compounds.
Description

The present invention relates to novel acrylates, fungicides containing them and their use as fungicides.
It is known that N-tridecyl-2,6-dimethylmorpholine or its salts, for example the acetate, can be used as fungicides (DE-1 164 152 and DE-1 173 722). It is also known that methyl .alpha.-phenyl-.beta.-methoxyacrylate derivatives (DE-3 519 282.8) can be used as fungicides.
However, their action is insufficient in some cases.
We have found that novel acrylates of the formula ##STR3## where R.sup.1 and R.sup.2 are identical or different and are each halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -alkylthio, oxiranyl which is unsubstituted or substituted by halogen, hydroxyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl or C.sub.1 -C.sub.3 -haloalkoxy, or R.sup.1 and R.sup.2 together form an unsaturated or saturated 3-membered to 6-membered ring which may contain 1 to 3 heteroatoms O or S(O).sub.m (where m is 0, 1 or 2) and is unsubstituted or substituted by halogen, hydroxyl, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl or oxo, the radicals X are identical or different and are each hydrogen, halogen, cyano, nitro, unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted C.sub.1 -C.sub.4 -alkoxy, or unsubstituted or substituted halo-C.sub.1 -C.sub.4 -alkyl, n is from 1 to 4, Y is unsubstituted or substituted C.sub.1 -C.sub.4 -alkylene, alkylene, C.sub.2 -C.sub.4 -alkenylene, C.sub.2 -C.sub.4 -alkynylene, O, S(O).sub.p (where p is 0, 1 or 2), unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted N, oxycarbonyl, carbonyloxy, carbonyloxy-C.sub.1 -C.sub.4 -alkylene, oxycarbonyl-C.sub.1 -C.sub.4 -alkylene, oxy-C.sub.1 -C.sub.4 -alkylene, thio-C.sub.1 -C.sub.4 -alkylene, azo, carbonylamino, aminocarbonyl, ##STR4## methyleneoxy or methylenethio, and Z is hydrogen, a cycloalkyl, aryl, arylalkyl, aralkenyl, aralkoxy, aryloxy, aryloxyalkyl, hetaryl, alkoxy, alkoxyalkyl, alkylthio or haloalkyl, these radicals being unsubstituted or substituted by halogen, cyano, nitro, alkyl, alkenyl, haloalkenyl, alkoxy, haloalkyl, unsubstituted or substituted phenyl or alkoxycarbonyl, have a very good fungicidal action.
The novel compounds of the formula I may be obtained in the preparation in the form of mixtures of stereoisomers (E,Z-isomers, diastereomers or enantiomers), which can be separated into the individual components in a conventional manner, for example by crystallization or chromatography. Both the individual isomers and their mixtures can be used as fungicides and form the subject of the invention.
R.sup.1 and R.sup.2 are identical or different and are each preferably methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, ##STR5## OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 :, SCH.sub.3 ;, SCH.sub.2 H.sub.5 or CF.sub.3, or R.sup.1 and R.sup.2 together are preferably --(CH.sub.2)-.sub.q (where q is 3, 4 or 5), --CH.dbd.CH--CH.dbd.CH--, O(CH.sub.2).sub.2 O--, --O(CH.sub.2).sub.3 O--, --OCH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 O--, --S(CH.sub.2).sub.2 S--, --S(CH.sub.2).sub.3 S--, ##STR6## or --CH.sub.2 (CH.sub.2).sub.2).sub.2 --.
n is preferably zero.
Y is preferably methylene, ethylene, ethenylene, ethynylene, O, S, methyleneoxy, oxymethylene, carbonyloxy, oxycarbonyl or ##STR7## and Z is preferably hydrogen, C.sub.1 -C.sub.16 -alkyl, C.sub.2 -C.sub.16 -alkenyl, C.sub.2 -C.sub.16 -alkynyl (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2,2-dimethylpropyl, 2-ethylhex-1-yl, 2,6-dimethylhept-1-yl , 2,6,10-trimethylundec- yl, allyl, prenyl, geranyl, 2,3-dihydrogeranyl, tetrahydrogeranyl, 2,6-dimethylhepta-1,5-dien-1yl, 2,6-dimethylhept-5-en- 1-yl or 2-ethylhex-1-en-1-yl), which are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy or halogen, or Z is furthermore preferably C.sub.3 -C.sub.12 -cycloalkyl which is substituted by C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 -alkoxy (e.g. cyclohexyl, cyclopropyl, in particular 1-methylcyclopropyl, 2-methylcyclopropyl or 2-dichlorocyclopropyl or 2,2-dichloro-1-methylcyclopropyl (A1), 2,2-dichloro-3,3-dimethylcyclopropyl (A2), 2,2,3,3-tetramethylcyclopropyl (A3), 2-(2'-methyl-1'-propenyl)-3,3-dimethylcyclopropyl (A4), 2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl (A5), 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl (A6), 2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl (A7), 2-phenylcyclopropyl (A8), 2-(4-chlorophenyl)-cyclopropyl (A9), 2,2-dichloro-3-phenylcyclopropyl (A10) or 2-carbomethoxycyclopropyl (A11)), or is furthermore preferably aryl, in particular phenyl, phenoxyphenyl, phenylphenyl, C.sub.1 -C.sub.4 -alkoxyphenyl, trifluoromethyl-phenyl, halophenyl or C.sub.1 -C.sub.4 -alkylphenyl (e.g. 2-fluoro-, 3-fluoro-, 4-fluoro-, 2-chloro-, 3-chloro-, 4-chloro-, 6-fluoro-, 2,4-dichloro-, 2,6-dichloro-, 3,5-dichloro-, 2,4,6-trichloro-, 2-bromo-, 4-bromo-, 2-methyl-3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2,4,6-trimethyl-, 4-tert-butyl-, 2-methoxy-, 3-methoxy-, 4-methoxy-, 2,3-dimethoxy-, 2-CF.sub.3 -, 3-CF.sub.3, 4-CF.sub.3 -, 3-tert-butoxy-, 4-tert-butoxy-, 4-phenoxy-, 4p-henylphenyl or naphthyl (1- or 2-naphthyl)), aryloxy (e.g. phenoxy), aralkyl, phenyl-C.sub.1 -C.sub.4 -alkyl (e.g. benzyl, halobenzyl, C.sub.1 -C.sub.4 -alkylbenzyl, 2-chlorobenzyl, 2-methylbenzyl, 2-phenylethyl, 3-phenylpropyl or 4-phenylbutyl), aralkenyl (e.g. styryl, halostyryl, C.sub.1 -C.sub.4 -alkylstyryl, ortho-chlorostyryl or para-tert-butylstyryl), hetaryl having 5 or 6 ring members and nitrogen, oxygen or sulfur as heteroatoms (e.g. 2-pyridyl-, 2-pyrimidyl-, 2-furyl- or 2-thiophenyl-), aryloxy-C.sub.1 -C.sub.4 -alkyl (e.g. phenoxyethyl or 4-phenoxybutyl), halo-C.sub.1 -C.sub.4 -alkyl (e.g. trifluoromethyl or trichloromethyl), halo-C.sub.1 -C.sub.4 -alkoxy, (e.g. trifluoromethoxy or trichloromethoxy).
The compounds of the formula I can be prepared, for example, by the reactions shown in scheme 1. ##STR8##
The .alpha.-ketocarboxylic esters of the formula II can be converted by a Wittig reaction with a disubstituted phosphonium halide in a conventional manner in the presence of a base, e.g. n-butyllithium, potassium tertbutylate, sodium hydride or sodium methylate, into the acrylate of the formula I (cf. R. Raap, Can. J. Chem. 49 (1971), 2143).
Ylides of the formula III likewise react with ketones to give products of the formula I (cf. G. Wittig and U. Schollkopf, Org. Synth. Coll., Vol. V 751 (1973)).
The reaction of a phenylchlorocarbene V with a silylenol ester in the presence of a free radical acceptor in a conventional manner (N. Slougui and G. Rousseau, Synth. Commun. 12 (5) (1982), 401) gives .beta.-disubstituted acrylates of the formula I.
The ester derivatives of the formula I are also obtained by Perkin condensation of a phenylacetic acid with a ketone in the presence of acetic anhydride and a base (cf. Johnson, Org. Reactions 1 (1942), 210) with subsequent esterification.
The preparation of the .alpha.-ketoesters of the formula II is known (EP 178862). For example, the aromatic Grignard compounds VI are reacted with imidazolides of the formula VII (J. S. Nimitz and H. S. Mosher, J. Org. Chem. 46 (1981), 211), the radicals X.sub.n, Y, Z and R having the abovementioned meanings. ##STR9##
The derivatives of the formula II where Y is oxymethylene, thiomethylene or carboxymethylene and n is 0 are advantageously prepared in the manner shown in Scheme 2. ##STR10##
.alpha.-Ketoesters of the formula VIII can be converted into the benzyl bromides of the formula IX with bromine or N-bromosuccinimide (NBS) in, for example, tetrachloromethane, if necessary with exposure to a light source of suitable wavelength (e.g. Hg vapor lamp, 300 watt) (cf. Horner and Winkelmann, Angew. Chem. 71 (1959), 349).
The novel .alpha.-ketocarboxylic esters of the formula IX are useful intermediates. They can be converted, for example, into the derivatives of the formula X by reacting them with an alkali metal salt, alkaline earth metal salt or ammonium salt of a carboxylic acid of the formula XI, where Z has the abovementioned meanings, in a solvent or diluent, e.g. acetone, acetonitrile, dimethyl sulfoxide, dioxan, dimethylformamide, N-methylpyrrolidone, N,N'-dimethylpropyleneurea or pyridine, with or without the addition of a catalyst, for example 0.01-10% by weight, based on composition X, of tetramethylethylenediamine or potassium iodide.
The acrylate derivates of the general formula XII can be prepared by the reactions shown in Scheme 3. ##STR11## (R.sup.3 and R.sup.4 are each alkyl or alkylene; see Table 3)
Ketene mercaptals of the formula XII can be prepared by alkylation of the dithiocarboxylic acid salts obtainable from phenylacetic esters (IV) and carbon disulfide (cf. R. Gompper and W. Topfl, Chem. Ber. 95 (1962), 2861, and Ann. Chem. 659 (1962), 90) or by reacting trithiocarbonates with active methylene components (cf. R. Gompper and E. Kutter, Chem. Ber. 98 (1965), 1365).
They are converted into the .beta.,.beta.-dichloroacrylates of the formula XIII using phosphorus pentachloride (cf. R. Gompper et al., Angew. Chem. 76 (1964), 583).
The conversion of these activated dichloromethylenes into the ketene acetals of the formula XIV is achieved by reaction with an alcoholate (cf. S. M. McElvain and H. F. McShane, J. Amer. Chem. Soc. 74 (1952), 2662).
Another method of obtaining the .beta.,.beta.-dialkoxyacrylates of the formula XIV is the base-catalyzed elimination of alcohol from the orthocarboxylic triesters of the formula XV or XVI (cf. S. M. McElvain et al., J. Amer. Chem. Soc. 73 (1951), 206, ibid, 71 (1949), 47); in the case of arylketene acetals (XVII) acylation with methyl chloroformate is subsequently carried out (cf. S. M. McElvain and R. D. Mullineaux, J. Amer. Chem. Soc. 74 (1952), 1811).





The Examples which follow illustrate the preparation of the novel compounds of the formula I:
1. Preparation of methyl 3-methyl-2-[2'-(.alpha.-methylcyclopropylcarboxymethylene)-phenyl]-2-butenoate (No. 280, Table 1)
(a) Preparation of methyl orthobromoethylphenylglyoxylate
50.0 g (0.28 mole) of methyl orthomethylphenylglyoxylate are dissolved together with 50.0 g (0.28 mole) of freshly crystallized N-bromosuccinimide in 3 1 of carbon tetrachloride. The mixture is exposed to a 300 W Hg vapor lamp for one hour, the reaction mixture is evaporated down to about 1 l and the organic phase is washed with 3.times.200 ml of water. The organic phase is dried over sodium sulfate and the solvent is distilled off, after which the residue is chromatographed over silica gel using 1:9 methyl tert-butyl ether/hexane to give 10 g of ketoester (II, YZ=CH.sub.3), and 21.1 g of benzyl bromide (II, YZ=CH.sub.2 Br) (37%, based on converted ketoester) as a yellow oil.
1.sub.H (CDCl.sub.3).delta.=3.97(s,3H), 4.90(s,2H), 7.4-7.8(m,4H).
IR (Film): 2955; 1740, 1690; 1435, 1318, 1207, 999 cm.sup.-1.
(b) Preparation of methyl ortho-(.alpha.-methylcyclopropylcarboxymethylene)-phenylglyoxylate
13.8 g (0.1 mole) of the potassium salt of .alpha.-methylcyclopropanecarboxylic acid are dissolved together with 21.1 g (0.082 mole) of ortho-(bromomethyl)-phenylglyoxylic acid and 0.3 g of potassium iodide in 300 ml of N-methylpyrrolidone. The mixture is stirred for 15 hours at 23.degree. C., poured onto 300 ml of ice water and extracted with 3.times.200 ml of methyl tert-butyl ether. The organic phases are washed with water, dried with sodium sulfate and evaporated down to give 24.0 g (106%) of chromatographically pure ester, which is used in the subsequent reaction.
1.sub.H (CDCl.sub.3): .delta.=0.70(m,2H), 1.27(m,2H), 1.35(s,3H), 3.96(s,3H), 5.46(s,2H), 7.4-7.8(m,4H).
(c) Preparation of methyl 3-methyl-2-[2'-(.alpha.-methylcyclopropylcarboxymethylene)-phenyl]-2-butenoate (No. 280, Table 1)
13.8 g (0.032 mole) of isopropyltriphenylphosphonium iodide in 100 ml of anhydrous tetrahydrofuran are initially taken under nitrogen. 20 ml of a 1.6 molar solution of n-butyllithium in hexane are added dropwise at 0.degree. C. After 1 hour at 0.degree. C., 8.0 g (0.029 mole) of methyl ortho-(.alpha.-methylcyclopropylcarboxymethylene)-phenylglyoxylate dissolved in 40 ml of anhydrous tetrahydrofuran are added dropwise. The mixture is allowed to warm to 23.degree. C. and is stirred for a further 2 hours, poured onto saturated ammonium chloride solution and extracted with methyl tert-butyl ether. The organic phases are washed with water, dried over sodium sulfate and evaporated down. The crude product is separated by column chromatography over silica gel using 1:9 methyl tert-butyl ether/hexane. 1.9 g (22%) of the abovementioned ester are obtained as an oil.
1.sub.H (CDCl.sub.3): .delta.=0.65(m,2H), 1.25(m,2H), 1.30(s,3H), 1.60(s,3H), 2.25(s,3H), 3.65(s,3H), 5.00(s,2H), 7.0-7.5(m,4H).
(Film): 1720, 1630, 1322, 1222, 1156, 1090, 755 cm.sup.-2.
Preparation of methyl 3-methyl-2-[2'-(2"-methylbenzyloxy-phenyl]-2-butenoate (No. 73, Table 1)
8.64 g (20 millimoles) of isopropylphosphonium iodide in 50 ml of anhydrous tetrahydrofuran are initially taken at 0.degree. C. under nitrogen. 8.3 ml of 2.5 M n-butyllithium solution in hexane are added dropwise at 0.degree. C. After 30 minutes at this temperature, 5.8 g (20 millimoles) of methyl 2-(2'-methylbenzyloxy)-phenylglyoxylate in 15 ml of anhydrous tetrahydrofuran are added all at once. Stirring is continued for 15 hours at room temperature (23.degree. C.), the mixture is evaporated down in a rotary evaporator and the residue is partitioned between saturated ammonium chloride solution and 1:1 methyl tert-butyl ether/hexane. Extraction of the aqueous phase 3 times with this solvent mixture, drying of the organic phases over sodium sulfate and evaporation give a crude product, which is separated by column chromatography over silica gel using 1:2 methyl tert-butyl ether/hexane. 3.3 g (53%) of the abovementioned ester are obtained as a pale yellow oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.=1.67(s,3H), 2.22(s,3H), 2.40 (s,3H), 3.57(s,3H), 5.05 (s,3H), 6.9-7.4(m,8H).
IR (Film): 1714, 1600, 1490, 1449, 1302, 1270, 1224, 1088, 752 cm.sup.-1
The compounds listed in the Tables below can be prepared in a similar manner.
TABLE 1__________________________________________________________________________ ##STR12##No. R.sup.1 R.sup.2 Y Z Data__________________________________________________________________________1 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.52 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2-FC.sub.6 H.sub.43 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 3-FC.sub.6 H.sub.44 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-FC.sub.6 H.sub.45 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2-ClC.sub.6 H.sub.46 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 3-ClC.sub.6 H.sub.47 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-ClC.sub.6 H.sub.48 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2Cl,6FC.sub.6 H.sub.39 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2,4-Cl.sub.2C.sub.6 H.sub.310 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2,6-Cl.sub.2C.sub.6 H.sub.311 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 3,5-Cl.sub.2C.sub.6 H.sub.312 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2,4,6-Cl.sub.3C.sub.6 H.sub.213 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2-CH.sub.3C.sub.6 H.sub.414 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 3-CH.sub.3C.sub.6 H.sub.415 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-CH.sub.3C.sub.6 H.sub.416 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.417 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.318 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.319 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.220 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2-OCH.sub.3C.sub.6 H.sub.421 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 3-OCH.sub.3C.sub.6 H.sub.422 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-OCH.sub.3C.sub.6 H.sub.423 CH.sub.3 CH.sub.3 CH.sub. 2 CH.sub.2 2-CF.sub.3C.sub.6 H.sub.424 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 3-CF.sub.3C.sub.6 H.sub.425 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-CF.sub.3C.sub.6 H.sub.426 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.427 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-OC.sub.6 H.sub.5C.sub.6 H.sub.428 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-C.sub.6 H.sub.5C.sub.6 H.sub.429 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 2-BrC.sub.6 H.sub.430 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 4-BrC.sub.6 H.sub.431 CH.sub.3 CH.sub.3 CHCH C.sub.6 H.sub.532 CH.sub.3 CH.sub.3 CHCH 2-FC.sub.6 H.sub.433 CH.sub.3 CH.sub.3 CHCH 3-FC.sub.6 H.sub.434 CH.sub.3 CH.sub.3 CHCH 4-FC.sub.6 H.sub.435 CH.sub.3 CH.sub.3 CHCH 2-ClC.sub.6 H.sub.436 CH.sub.3 CH.sub.3 CHCH 3-ClC.sub.6 H.sub.437 CH.sub.3 CH.sub.3 CHCH 4-ClC.sub.6 H.sub.438 CH.sub.3 CH.sub.3 CHCH 2Cl,6FC.sub.6 H.sub.339 CH.sub.3 CH.sub.3 CHCH 2,4-Cl.sub.2C.sub.6 H.sub.340 CH.sub.3 CH.sub.3 CHCH 2,6-Cl.sub.2C.sub.6 H.sub.341 CH.sub.3 CH.sub.3 CHCH 3,5-Cl.sub.2C.sub.6 H.sub.342 CH.sub.3 CH.sub.3 CHCH 2,4,6-Cl.sub.3C.sub.6 H.sub.243 CH.sub.3 CH.sub.3 CHCH 2-CH.sub.3C.sub.6 H.sub.444 CH.sub.3 CH.sub.3 CHCH 3-CH.sub.3C.sub.6 H.sub.445 CH.sub.3 CH.sub.3 CHCH 4-CH.sub.3C.sub.6 H.sub.446 CH.sub.3 CH.sub.3 CHCH 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.447 CH.sub.3 CH.sub.3 CHCH 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.348 CH.sub.3 CH.sub.3 CHCH 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.349 CH.sub.3 CH.sub.3 CHCH 2,4,6-(CH.sub.3).sub.3C.sub. 6 H.sub.250 CH.sub.3 CH.sub.3 CHCH 2-OCH.sub.3C.sub.6 H.sub.451 CH.sub.3 CH.sub.3 CHCH 3-OCH.sub.3C.sub.6 H.sub.452 CH.sub.3 CH.sub.3 CHCH 4-OCH.sub.3C.sub.6 H.sub.453 CH.sub.3 CH.sub.3 CHCH 2-CF.sub.3C.sub.6 H.sub.454 CH.sub.3 CH.sub.3 CHCH 3-CF.sub.3C.sub.6 H.sub.455 CH.sub.3 CH.sub.3 CHCH 4-CF.sub.3C.sub.6 H.sub.456 CH.sub.3 CH.sub.3 CHCH 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.457 CH.sub.3 CH.sub.3 CHCH 4-O-C.sub.6 H.sub.5C.sub.6 H.sub.458 CH.sub.3 CH.sub.3 CHCH 4-C.sub.6 H.sub.5C.sub.6 H.sub.459 CH.sub.3 CH.sub.3 CHCH 2-BrC.sub.6 H.sub.460 CH.sub.3 CH.sub.3 CHCH 4-BrC.sub.6 H.sub.461 CH.sub.3 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.562 CH.sub.3 CH.sub.3 CH.sub.2 O 2-FC.sub.6 H.sub. 463 CH.sub.3 CH.sub.3 CH.sub.2 O 3-FC.sub.6 H.sub.464 CH.sub.3 CH.sub.3 CH.sub.2 O 4-FC.sub.6 H.sub.465 CH.sub.3 CH.sub.3 CH.sub.2 O 2-ClC.sub.6 H.sub.466 CH.sub.3 CH.sub.3 CH.sub.2 O 3-ClC.sub.6 H.sub.467 CH.sub.3 CH.sub.3 CH.sub.2 O 4-ClC.sub.6 H.sub.468 CH.sub.3 CH.sub.3 CH.sub.2 O 2Cl,6FC.sub.6 H.sub.369 CH.sub.3 CH.sub.3 CH.sub.2 O 2,4-Cl.sub.2C.sub.6 H.sub.370 CH.sub.3 CH.sub.3 CH.sub.2 O 2,6-Cl.sub.2C.sub.6 H.sub.371 CH.sub.3 CH.sub.3 CH.sub.2 O 3,5-Cl.sub.2C.sub.6 H.sub.372 CH.sub.3 CH.sub.3 CH.sub.2 O 2,4,6-Cl.sub.3C.sub.6 H.sub.273 CH.sub.3 CH.sub.3 CH.sub.2 O 2-CH.sub.3C.sub.6 H.sub.4 oil; IR(film): 1713, 1630, 1276, 1215, 1112, 1092, 758, 70874 CH.sub.3 CH.sub.3 CH.sub.2 O 3-CH.sub.3C.sub.6 H.sub.475 CH.sub.3 CH.sub.3 CH.sub.2 O 4-CH.sub.3C.sub.6 H.sub.476 CH.sub.3 CH.sub.3 CH.sub.2 O 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.477 CH.sub.3 CH.sub.3 CH.sub.2 O 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.378 CH.sub.3 CH.sub.3 CH.sub.2 O 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.379 CH.sub.3 CH.sub.3 CH.sub.2 O 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.280 CH.sub.3 CH.sub.3 CH.sub.2 O 2-OCH.sub.3C.sub.6 H.sub.481 CH.sub.3 CH.sub.3 CH.sub.2 O 3-OCH.sub.3C.sub.6 H.sub.482 CH.sub.3 CH.sub.3 CH.sub.2 O 4-OCH.sub.3C.sub.6 H.sub.483 CH.sub.3 CH.sub.3 CH.sub.2 O 2-CF.sub.3C.sub.6 H.sub.484 CH.sub.3 CH.sub.3 CH.sub.2 O 3-CF.sub.3C.sub.6 H.sub.485 CH.sub.3 CH.sub.3 CH.sub.2 O 4-CF.sub.3C.sub.6 H.sub.486 CH.sub.3 CH.sub.3 CH.sub.2 O 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.487 CH.sub.3 CH.sub.3 CH.sub.2 O 4-OC.sub.6 H.sub.5C.sub.6 H.sub.488 CH.sub.3 CH.sub.3 CH.sub.2 O 4-C.sub.6 H.sub.5C.sub.6 H.sub.489 CH.sub.3 CH.sub.3 CH.sub.2 O 2-BrC.sub.6 H.sub.490 CH.sub.3 CH.sub.3 CH.sub.2 O 4-BrC.sub.6 H.sub.491 CH.sub.3 CH.sub.3 OCH.sub.2 C.sub.6 H.sub.592 CH.sub.3 CH.sub.3 OCH.sub.2 2-FC.sub.6 H.sub.493 CH.sub.3 CH.sub.3 OCH.sub.2 3-FC.sub.6 H.sub.494 CH.sub.3 CH.sub.3 OCH.sub.2 4-FC.sub.6 H.sub.495 CH.sub.3 CH.sub.3 OCH.sub.2 2-ClC.sub.6 H.sub.496 CH.sub.3 CH.sub.3 OCH.sub.2 3-ClC.sub.6 H.sub.497 CH.sub.3 CH.sub.3 OCH.sub.2 4-ClC.sub.6 H.sub.498 CH.sub.3 CH.sub.3 OCH.sub.2 2Cl,6FC.sub.6 H.sub.399 CH.sub.3 CH.sub.3 OCH.sub.2 2,4-Cl.sub.2C.sub.6 H.sub.3100 CH.sub.3 CH.sub.3 OCH.sub.2 2,6-Cl.sub.2C.sub.6 H.sub.3101 CH.sub.3 CH.sub.3 OCH.sub.2 3,5-Cl.sub.2C.sub.6 H.sub.3102 CH.sub.3 CH.sub.3 OCH.sub.2 2,4,6-Cl.sub.3C.sub.6 H.sub.2103 CH.sub.3 CH.sub.3 OCH.sub.2 2-CH.sub.3C.sub.6 H.sub.4104 CH.sub.3 CH.sub.3 OCH.sub.2 3-CH.sub.3C.sub.6 H.sub.4105 CH.sub.3 CH.sub.3 OCH.sub.2 4-CH.sub.3C.sub.6 H.sub.4106 CH.sub.3 CH.sub.3 OCH.sub.2 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4107 CH.sub.3 CH.sub.3 OCH.sub.2 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3108 CH.sub.3 CH.sub.3 OCH.sub.2 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3109 CH.sub.3 CH.sub.3 OCH.sub.2 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2110 CH.sub.3 CH.sub.3 OCH.sub.2 2-OCH.sub.3C.sub.6 H.sub.4111 CH.sub.3 CH.sub.3 OCH.sub.2 3-OCH.sub.3C.sub.6 H.sub.4112 CH.sub.3 CH.sub.3 OCH.sub.2 4-OCH.sub. 3C.sub.6 H.sub.4113 CH.sub.3 CH.sub.3 OCH.sub.2 2-CF.sub.3C.sub.6 H.sub.4114 CH.sub.3 CH.sub.3 OCH.sub.2 3-CF.sub.3C.sub.6 H.sub.4115 CH.sub.3 CH.sub.3 OCH.sub.2 4-CF.sub.3C.sub.6 H.sub.4116 CH.sub.3 CH.sub.3 OCH.sub.2 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4117 CH.sub.3 CH.sub.3 OCH.sub.2 4-OC.sub.6 H.sub.5C.sub.6 H.sub.4118 CH.sub.3 CH.sub.3 OCH.sub.2 4-C.sub.6 H.sub.5C.sub.6 H.sub.4119 CH.sub.3 CH.sub.3 OCH.sub.2 2-BrC.sub.6 H.sub.4120 CH.sub.3 CH.sub.3 OCH.sub.2 4-BrC.sub.6 H.sub.4121 CH.sub.3 CH.sub.3 SCH.sub.2 C.sub.6 H.sub.5122 CH.sub.3 CH.sub.3 SCH.sub.2 2-FC.sub.6 H.sub.4123 CH.sub.3 CH.sub.3 SCH.sub.2 3-FC.sub.6 H.sub.4124 CH.sub.3 CH.sub.3 SCH.sub.2 4-FC.sub.6 H.sub.4125 CH.sub.3 CH.sub.3 SCH.sub.2 2-ClC.sub.6 H.sub.4126 CH.sub.3 CH.sub.3 SCH.sub.2 3-ClC.sub.6 H.sub.4127 CH.sub.3 CH.sub.3 SCH.sub.2 4-ClC.sub.6 H.sub.4128 CH.sub.3 CH.sub.3 SCH.sub.2 2Cl,6FC.sub.6 H.sub.3129 CH.sub.3 CH.sub.3 SCH.sub.2 2,4-Cl.sub.2C.sub.6 H.sub.3130 CH.sub.3 CH.sub.3 SCH.sub.2 2,6-Cl.sub.2C.sub.6 H.sub.3131 CH.sub.3 CH.sub.3 SCH.sub.2 3,5-Cl.sub.2C.sub.6 H.sub.3132 CH.sub.3 CH.sub.3 SCH.sub.2 2,4,6-Cl.sub.3C.sub.6 H.sub.2133 CH.sub.3 CH.sub.3 SCH.sub.2 2-CH.sub.3C.sub.6 H.sub.4134 CH.sub.3 CH.sub.3 SCH.sub.2 3-CH.sub.3C.sub.6 H.sub.4135 CH.sub.3 CH.sub.3 SCH.sub.2 4-CH.sub.3C.sub.6 H.sub.4136 CH.sub.3 CH.sub.3 SCH.sub.2 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4137 CH.sub.3 CH.sub.3 SCH.sub.2 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3138 CH.sub.3 CH.sub.3 SCH.sub.2 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3139 CH.sub.3 CH.sub.3 SCH.sub.2 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2140 CH.sub.3 CH.sub.3 SCH.sub.2 2-OCH.sub.3C.sub.6 H.sub.4141 CH.sub.3 CH.sub.3 SCH.sub.2 3-OCH.sub.3C.sub.6 H.sub.4142 CH.sub.3 CH.sub.3 SCH.sub.2 4-OCH.sub.3C.sub.6 H.sub.4143 CH.sub.3 CH.sub.3 SCH.sub.2 2-CF.sub.3C.sub.6 H.sub.4144 CH.sub.3 CH.sub.3 SCH.sub.2 3-CF.sub.3C.sub.6 H.sub.4145 CH.sub.3 CH.sub.3 SCH.sub.2 4-CF.sub.3C.sub.6 H.sub.4146 CH.sub.3 CH.sub.3 SCH.sub.2 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4147 CH.sub.3 CH.sub.3 SCH.sub.2 4-OC.sub.6 H.sub.5C.sub.6 H.sub.4148 CH.sub.3 CH.sub.3 SCH.sub.2 4-C.sub.6 H.sub.5C.sub.6 H.sub.4149 CH.sub.3 CH.sub.3 SCH.sub.2 2-BrC.sub.6 H.sub.4150 CH.sub.3 CH.sub.3 SCH.sub.2 4-BrC.sub.6 H.sub.4151 CH.sub.3 CH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5 mp.: 75.degree. C.; IR(KBr): 1713, 1630, 1276, 1215, 1112, 1092, 758, 708 cm.sup.-1152 CH.sub.3 CH.sub.3 COOCH.sub.2 2-FC.sub.6 H.sub.4153 CH.sub.3 CH.sub.3 COOCH.sub.2 3-FC.sub.6 H.sub.4154 CH.sub.3 CH.sub.3 COOCH.sub.2 4-FC.sub.6 H.sub.4155 CH.sub.3 CH.sub.3 COOCH.sub.2 2-ClC.sub.6 H.sub.4156 CH.sub.3 CH.sub.3 COOCH.sub.2 3-ClC.sub.6 H.sub.4157 CH.sub.3 CH.sub.3 COOCH.sub.2 4-ClC.sub.6 H.sub.4158 CH.sub.3 CH.sub.3 COOCH.sub.2 2Cl,6FC.sub.6 H.sub.3159 CH.sub.3 CH.sub.3 COOCH.sub.2 2,4-Cl.sub.2C.sub.6 H.sub.3160 CH.sub.3 CH.sub.3 COOCH.sub.2 2,6-Cl.sub.2C.sub.6 H.sub.3161 CH.sub.3 CH.sub.3 COOCH.sub.2 3,5-Cl.sub.2C.sub.6 H.sub.3162 CH.sub.3 CH.sub.3 COOCH.sub.2 2,4,6-Cl.sub.3C.sub.6 H.sub.2163 CH.sub.3 CH.sub.3 CO OCH.sub.2 2-CH.sub.3C.sub.6 H.sub.4164 CH.sub.3 CH.sub.3 COOCH.sub.2 3-CH.sub.3C.sub.6 H.sub.4165 CH.sub.3 CH.sub.3 COOCH.sub.2 4-CH.sub.3C.sub.6 H.sub.4166 CH.sub.3 CH.sub.3 COOCH.sub.2 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4167 CH.sub.3 CH.sub.3 COOCH.sub.2 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3168 CH.sub.3 CH.sub.3 COOCH.sub.2 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3169 CH.sub.3 CH.sub.3 COOCH.sub.2 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2170 CH.sub.3 CH.sub.3 COOCH.sub.2 2-OCH.sub.3C.sub.6 H.sub.4171 CH.sub.3 CH.sub.3 COOCH.sub.2 3-OCH.sub.3C.sub.6 H.sub.4172 CH.sub.3 CH.sub.3 COOCH.sub.2 4-OCH.sub.3C.sub.6 H.sub.4173 CH.sub.3 CH.sub.3 COOCH.sub.2 2-CF.sub.3C.sub.6 H.sub.4174 CH.sub.3 CH.sub.3 COOCH.sub.2 3-CF.sub.3C.sub.6 H.sub.4175 CH.sub.3 CH.sub.3 CO OCH.sub.2 4-CF.sub.3C.sub.6 H.sub.4176 CH.sub.3 CH.sub.3 COOCH.sub.2 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4177 CH.sub.3 CH.sub.3 COOCH.sub.2 4-OC.sub.6 H.sub.5C.sub.6 H.sub.4178 CH.sub.3 CH.sub.3 COOCH.sub.2 4-C.sub.6 H.sub.5C.sub.6 H.sub.4179 CH.sub.3 CH.sub.3 COOCH.sub.2 2-BrC.sub.6 H.sub.4180 CH.sub.3 CH.sub.3 COOCH.sub.2 4-BrC.sub.6 H.sub.4181 CH.sub.3 CH.sub.3 CC C.sub.6 H.sub.5182 CH.sub.3 CH.sub.3 CC 2-ClC.sub.6 H.sub.4183 CH.sub.3 CH.sub.3 CC 3-ClC.sub.6 H.sub.4184 CH.sub.3 CH.sub.3 CC 4-ClC.sub.6 H.sub.4185 CH.sub.3 CH.sub.3 O C.sub.6 H.sub.5186 CH.sub.3 CH.sub.3 O 2-ClC.sub.6 H.sub.4187 CH.sub.3 CH.sub.3 O 3-ClC.sub.6 H.sub.4188 CH.sub.3 CH.sub.3 O 4-ClC.sub.6 H.sub.4189 CH.sub.3 CH.sub.3 O 2-CH.sub.3C.sub.6 H.sub.4190 CH.sub.3 CH.sub.3 O 4-CH.sub.3C.sub.6 H.sub.4191 CH.sub.3 CH.sub.3 O 4-C.sub.6 H.sub.5C.sub.6 H.sub.4192 CH.sub.3 CH.sub.3 O 1-C.sub.10 H.sub.7193 CH.sub.3 CH.sub.3 O CH.sub.3194 CH.sub.3 CH.sub.3 O CH.sub.2 CHCH.sub.2195 CH.sub.3 CH.sub.3 O CH.sub.2 CHC(CH.sub.3).sub.2196 CH.sub.3 CH.sub.3 O geranyl197 CH.sub.3 CH.sub.3 O tetrahydrogeranyl198 CH.sub.3 CH.sub.3 O 2-OCH.sub.3C.sub.6 H.sub.4199 CH.sub.3 CH.sub.3 O 2,3-(OCH.sub.3).sub.2C.sub.6 H.sub.3200 CH.sub.3 CH.sub.3 S C.sub.6 H.sub.5201 CH.sub.3 CH.sub.3 S 2-ClC.sub. 6 H.sub.4202 CH.sub.3 CH.sub.3 S 3-ClC.sub.6 H.sub.4203 CH.sub.3 CH.sub.3 S 4-ClC.sub.6 H.sub.4204 CH.sub.3 CH.sub.3 S 2-CH.sub.3C.sub.6 H.sub.4205 CH.sub.3 CH.sub.3 S 4-CH.sub.3C.sub.6 H.sub.4206 CH.sub.3 CH.sub.3 S 4-C.sub.6 H.sub.5C.sub.6 H.sub.4207 CH.sub.3 CH.sub.3 S CH.sub.3208 CH.sub.3 CH.sub.3 S geranyl209 CH.sub.3 CH.sub.3 S 2-pyridyl210 CH.sub.3 CH.sub.3 S 2-pyrimidyl211 CH.sub.3 CH.sub.3 COO C.sub.6 H.sub.5212 CH.sub.3 CH.sub.3 COO 2-ClC.sub.6 H.sub.4213 CH.sub.3 CH.sub.3 COO 3-ClC.sub.6 H.sub.4214 CH.sub.3 CH.sub.3 COO 4-ClC.sub.6 H.sub.4215 CH.sub.3 CH.sub.3 COO 2-CH.sub.3C.sub.6 H.sub.4216 CH.sub.3 CH.sub.3 COO 4-CH.sub.3C.sub.6 H.sub.4217 CH.sub.3 CH.sub.3 COO 4-C.sub.6 H.sub. 5C.sub.6 H.sub.4218 CH.sub.3 CH.sub.3 OCO C.sub.6 H.sub.5219 CH.sub.3 CH.sub.3 OCO 2-ClC.sub.6 H.sub.4220 CH.sub.3 CH.sub.3 OCO 3-ClC.sub.6 H.sub.4221 CH.sub.3 CH.sub.3 OCO 4-ClC.sub.6 H.sub.4222 CH.sub.3 CH.sub.3 OCO 2-CH.sub.3C.sub.6 H.sub.4223 CH.sub.3 CH.sub.3 OCO CH.sub.3224 CH.sub.3 CH.sub.3 OCO t-C.sub.4 H.sub.9225 CH.sub.3 CH.sub.3 OCO CH.sub.2 C.sub.6 H.sub.5226 CH.sub.3 CH.sub.3 HNCOO C.sub.6 H.sub.5227 CH.sub.3 CH.sub.3 HNCOO 2-ClC.sub.6 H.sub.4228 CH.sub.3 CH.sub.3 HNCOO 4-ClC.sub.6 H.sub.4229 CH.sub.3 CH.sub.3 HNCOO C.sub.6 H.sub.11230 CH.sub.3 CH.sub.3 HNCOO n-C.sub.4 H.sub.9231 CH.sub.3 CH.sub.3 CHCH CH.sub.2 C(CH.sub.3).sub.3232 CH.sub.3 CH.sub.3 CHCH CHC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2233 CH.sub.3 CH.sub.3 CHCH CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).su b.2234 CH.sub.3 CH.sub.3 CHCH CHC(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3235 CH.sub.3 CH.sub.3 CHCH CH.sub.2 CH(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3236 CH.sub.3 CH.sub.3 CHCH CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2237 CH.sub.3 CH.sub.3 CHCH cyclopropyl238 CH.sub.3 CH.sub.3 CHCH 1-methycyclopropyl239 CH.sub.3 CH.sub.3 CHCH CHCHC.sub.6 H.sub.5240 CH.sub.3 CH.sub.3 CHCH CH.sub.2CH.sub.2C.sub.6 H.sub.5241 CH.sub.3 CH.sub.3 CHCH C(CH.sub.3).sub.3242 CH.sub.3 CH.sub.3 CHCH cyclohexyl243 CH.sub.3 CH.sub.3 CHCH (CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2).sub.2 CH.sub.2 CH(CH.sub.3 ).sub.2244 CH.sub.3 CH.sub.3 CHCH 2-furyl245 CH.sub.3 CH.sub.3 CHCH 2-thiophenyl246 CH.sub.3 CH.sub.3 CHCH CF.sub.3247 CH.sub.3 CH.sub.3 CHCH CCl.sub.3248 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3249 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3250 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2251 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3252 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 (CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2).sub.2 CH.sub.2 CH(CH.sub.3).sub.2253 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 cyclopropyl254 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 1-methyl-cyclopropyl255 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl256 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5257 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5258 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CF.sub.3259 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CCl.sub.3260 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5261 CH.sub.3 CH.sub.3 CH.sub.2 O CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).su b.2262 CH.sub.3 CH.sub.3 CH.sub.2 O (CHC(CH.sub.3)CH.sub.2 CH.sub.2).sub.2 CHC(CH.sub.3).su b.2263 CH.sub.3 CH.sub.3 CH.sub.2 O (CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2).sub.2 CH.sub.2 CH(CH.sub.3).sub.2264 CH.sub.3 CH.sub.3 CH.sub.2 O CHCHC.sub.6 H.sub.5265 CH.sub.3 CH.sub.3 CH.sub.2 O CH.sub.2CH.sub.2 C.sub.6 H.sub.5266 CH.sub.3 CH.sub.3 CH.sub.2 O CH.sub.2OC.sub.6 H.sub.5267 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3268 CH.sub.3 CH.sub.3 OCH.sub.2 C.sub.2 H.sub.5269 CH.sub.3 CH.sub.3 OCH.sub.2 n-C.sub.3 H.sub.7270 CH.sub.3 CH.sub.3 OCH.sub.2 i-C.sub.3 H.sub.7271 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 CHCH.sub.2272 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2273 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 C.sub.6 H.sub.5274 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2(2-ClC.sub.6 H.sub.4)275 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 (2-CH.sub.3C.sub.6 H.sub.4)276 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5277 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5278 CH.sub.3 CH.sub.3 OCH.sub.2 (CH.sub.2).sub.4 OC.sub.6 H.sub.5279 CH.sub.3 CH.sub.3 COOCH.sub.2 cyclopropyl280 CH.sub.3 CH.sub.3 COOCH.sub.2 1-methylcyclopropyl oil; IR(film): 1720, 1322, 1222, 1156, 1090, 755 cm.sup.-1281 CH.sub.3 CH.sub.3 COOCH.sub.2 2-methylcyclopropyl282 CH.sub.3 CH.sub.3 COOCH.sub.2 2,2-dichlorocyclopropyl283 CH.sub.3 CH.sub.3 COOCH.sub.2 A1*284 CH.sub.3 CH.sub.3 COOCH.sub.2 A2*285 CH.sub.3 CH.sub.3 COOCH.sub.2 A3*286 CH.sub.3 CH.sub.3 COOCH.sub.2 A4*287 CH.sub.3 CH.sub.3 COOCH.sub.2 A5*288 CH.sub.3 CH.sub.3 COOCH.sub.2 A6*289 CH.sub.3 CH.sub.3 COOCH.sub.2 A7*290 CH.sub.3 CH.sub.3 COOCH.sub.2 A8*291 CH.sub.3 CH.sub.3 COOCH.sub.2 A9*292 CH.sub.3 CH.sub.3 COOCH.sub.2 A10*293 CH.sub.3 CH.sub.3 COOCH.sub.2 A11*294 CH.sub.3 CH.sub.3 COOCH.sub.2 CH.sub.3295 CH.sub.3 CH.sub.3 COOCH.sub.2 C.sub.2 H.sub.5296 CH.sub.3 CH.sub.3 COOCH.sub.2 n-C.sub.3 H.sub. 7297 CH.sub.3 CH.sub.3 COOCH.sub.2 i-C.sub.3 H.sub.7298 CH.sub.3 CH.sub.3 COOCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3299 CH.sub.3 CH.sub.3 COOCH.sub.2 tert-C.sub.4 H.sub.9 oil; IR(film): 1727, 1718, 1282, 1222, 1150, 1090, 754 cm.sup.-1300 CH.sub.3 CH.sub.3 COOCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3301 CH.sub.3 CH.sub.3 COOCH.sub.2 CH(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3302 CH.sub.3 CH.sub.3 COOCH.sub.2 CH(iso-C.sub.3 H.sub.7)CH.sub.2 CH.sub.2 CH(CH.sub.3).s ub.2303 CH.sub.3 CH.sub.3 COOCH.sub.2 CHCHC.sub.6 H.sub.5304 CH.sub.3 CH.sub.3 COOCH.sub.2 CHCH-(2-chloro)-C.sub.6 H.sub.4305 CH.sub.3 CH.sub.3 COOCH.sub.2 CHCH-(4-tert.butyl)-C.sub.6 H.sub.4306 CH.sub.3 CH.sub.3 COOCH.sub.2 CH.sub.2 CH.sub.2C.sub.6 H.sub.5307 CH.sub.3 CH.sub.3 COOCH.sub.2 (CH.sub.2).sub.4 C.sub.6 H.sub.5308 CH.sub.3 CH.sub.3 COOCH.sub.2 CH.sub.2 CH.sub.2OC.sub.6 H.sub.5309 CH.sub.3 CH.sub.3 COOCH.sub.2 (CH.sub.2).sub.4OC.sub.6 H.sub.5310 CH.sub.3 CH.sub.3 COOCH.sub.2 CH(Cl)C.sub.6 H.sub.5__________________________________________________________________________ *for formulae see previous text
TABLE 2__________________________________________________________________________ ##STR13##No. R.sup.1 R.sup.2 Y Z Data__________________________________________________________________________ 1a Cl Cl CHCH C.sub.6 H.sub.5 2a Cl Cl CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 3a Cl Cl OCH.sub.2 C.sub.6 H.sub.5 4a Cl Cl CH.sub.2O C.sub.6 H.sub.5 5a Cl Cl SCH.sub.2 C.sub.6 H.sub.5 6a Cl Cl O C.sub.6 H.sub.5 7a Br Br CHCH C.sub.6 H.sub.5 8a Br Br CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 9a Br Br OCH.sub.2 C.sub.6 H.sub.5 10a Br Br CH.sub.2 O C.sub.6 H.sub.5 11a Br Br SCH.sub.2 C.sub.6 H.sub.5 12a Br Br O C.sub.6 H.sub.5 13a C.sub.2 H.sub.5 C.sub.2 H.sub.5 CHCH C.sub.6 H.sub.5 14a C.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 15a C.sub.2 H.sub.5 C.sub.2 H.sub.5 OCH.sub.2 C.sub.6 H.sub.5 16a C.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.2 O C.sub.6 H.sub.5 17a C.sub.2 H.sub.5 C.sub.2 H.sub.5 SCH.sub.2 C.sub.6 H.sub.5 18a C.sub.2 H.sub.5 C.sub.2 H.sub.5 O C.sub.6 H.sub.5 19a C.sub.2 H.sub.5 C.sub.2 H.sub.5 OCH.sub.2 2-ClC.sub.6 H.sub.4 20a C.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.2 O 2-ClC.sub.6 H.sub.4 21a C.sub.2 H.sub.5 C.sub.2 H.sub.5 COOCH.sub.2 C.sub.6 H.sub.5 22a C.sub.2 H.sub.5 C.sub.2 H.sub.5 COOCH.sub.2 1-methylcyclopropyl 23a C.sub.2 H.sub.5 C.sub.2 H.sub.5 COOCH.sub.2 t-C.sub.4 H.sub.9 24a C.sub.2 H.sub.5 C.sub.2 H.sub.5 COOCH.sub.2 2,2-dichlorocyclopropyl 25a C.sub.2 H.sub.5 C.sub.2 H.sub.5 COOCH.sub.2 CH(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 26a C.sub.2 H.sub.5 C.sub.2 H.sub.5 COOCH.sub.2 CHCHC.sub.6 H.sub.5 27a C.sub.2 H.sub.5 C.sub.2 H.sub.5 COOCH.sub.2 A1* 28a C.sub.2 H.sub.5 C.sub.2 H.sub.5 COOCH.sub.2 A6* 29a n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7 CHCH C.sub.6 H.sub.5 30a n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 31a n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7 CH.sup.2 O C.sup.6 H.sup.5 32a n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7 OCH.sub.2 C.sub.6 H.sub.5 33a n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7 COOCH.sup.2 C.sup.6 H.sup.5 34a OCH.sub.3 OCH.sub.3 CHCH C.sub.6 H.sub.5 35a OCH.sub.3 OCH.sub.3 CHCH 3-ClC.sub.6 H.sub.4 36a OCH.sub.3 OCH.sub.3 CHCH 3-CF.sub.3C.sub.6 H.sub.4 37a OCH.sub.3 OCH.sub.3 CHCH 2-CH.sub.3C.sub.6 H.sub.4 38a OCH.sub.3 OCH.sub.3 CHCH 3-CH.sub.3C.sub.6 H.sub.4 39a OCH.sub.3 OCH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 40a OCH.sub.3 OCH.sub.3 CH.sub.2 CH.sub.2 3-ClC.sub.6 H.sub.4 41a OCH.sub.3 OCH.sub.3 CH.sub.2 CH.sub.2 3-CF.sub.3C.sub.6 H.sub.4 42a OCH.sub.3 OCH.sub.3 CH.sub.2 CH.sub.2 3-CH.sub.3C.sub.6 H.sub.4 43a OCH.sub.3 OCH.sub.3 CH.sub.2 CH.sub.2 2-ClC.sub.6 H.sub.4 44a OCH.sub.3 OCH.sub.3 CH.sub.2 O C.sub.6 H.sub.5 45a OCH.sub.3 OCH.sub.3 CH.sub.2 O 3-ClC.sub.6 H.sub.4 46a OCH.sub.3 OCH.sub.3 CH.sub.2 O 2,4-Cl.sub.2C.sub.6 H.sub.3 47a OCH.sub.3 OCH.sub.3 CH.sub.2 O 2-BrC.sub.6 H.sub.4 48a OCH.sub.3 OCH.sub.3 OCH.sub.2 C.sub.6 H.sub.5 49a OCH.sub.3 OCH.sub.3 OCH.sub.2 3-ClC.sub.6 H.sub.4 50a OCH.sub.3 OCH.sub.3 OCH.sub.2 2,4-Cl.sub.2C.sub.6 H.sub.3 51a OCH.sub.3 OCH.sub.3 OCH.sub.2 2-BrC.sub.6 H.sub.4 52a OCH.sub.3 OCH.sub.3 SCH.sub.2 C.sub.6 H.sub.5 53a OCH.sub.3 OCH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5 54a OCH.sub.3 OCH.sub.3 COOCH.sub.2 tert.-C.sub.4 H.sub.9 55a OCH.sub.3 OCH.sub.3 COOCH.sub.2 1-methylcyclopropyl 56a OCH.sub.3 OCH.sub.3 COOCH.sub.2 2,2-dichlorocyclopropyl 57a OCH.sub.3 OCH.sub.3 COOCH.sub.2 CH(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 58a OCH.sub.3 OCH.sub.3 COOCH.sub.2 CHCHC.sub.6 H.sub.5 59a OCH.sub.3 OCH.sub. 3 COOCH.sub.2 C.sub.6 H.sub.5 60a OCH.sub.3 OCH.sub.3 COOCH.sub.2 A1* 61a OCH.sub.3 OCH.sub.3 COOCH.sub.2 A6* 62a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 CHCH C.sub.6 H.sub.5 63a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 CH.sub.2CH.sub.2 C.sub.6 H.sub.5 64a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 CH.sub.2 O C.sub.6 H.sub.5 65a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 OCH.sub.2 C.sub.6 H.sub.5 66a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 SCH.sub.2 C.sub.6 H.sub.5 67a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 O C.sub.6 H.sub.5 68a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 COOCH.sub.2 C.sub.6 H.sub.5 69a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 COOCH.sub.2 1-methylcyclopropyl 70a OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 COOCH.sub.2 A1* 71a OC.sub.2 H.sub. 5 OC.sub.2 H.sub.5 COOCH.sub.2 A6* 72a CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH C.sub.6 H.sub.5 73a CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.2CH.sub.2 C.sub.6 H.sub.5 74a CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.2 O C.sub.6 H.sub.5 75a CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.2 C.sub.6 H.sub.5 76a CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3 SCH.sub.2 C.sub.6 H.sub.5 77a CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3 O C.sub.6 H.sub.5 78a CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5 79a CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3 COOCH.sub.2 1-methylcyclopropyl 80a SCH.sub.3 SCH.sub.3 CHCH C.sub.6 H.sub.5 81a SCH.sub.3 SCH.sub.3 CHCH 2-CH.sub.3C.sub.6 H.sub.4 82a SCH.sub.3 SCH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 83a SCH.sub.3 SCH.sub.3 CH.sub.2 CH.sub.2 3-ClC.sub.6 H.sub.4 84a SCH.sub.3 SCH.sub.3 CH.sub.2 CH.sub.2 3-CH.sub.3C.sub.6 H.sub.4 85a SCH.sub.3 SCH.sub.3 CH.sub.2 CH.sub.2 3-CF.sub.3C.sub.6 H.sub.4 86a SCH.sub.3 SCH.sub.3 CH.sub.2 O C.sub.6 H.sub.5 87a SCH.sub.3 SCH.sub.3 CH.sub.2 O 3-ClC.sub.6 H.sub.4 88a SCH.sub.3 SCH.sub.3 OCH.sub.2 C.sub.6 H.sub.5 89a SCH.sub.3 SCH.sub.3 SCH.sub.2 C.sub.6 H.sub.5 90a SCH.sub.3 SCH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5 91a SCH.sub.3 SCH.sub.3 COOCH.sub.2 1-methylcyclopropyl 92a SCH.sub.3 SCH.sub.3 COOCH.sub.2 A1* 93a SCH.sub.3 SCH.sub.3 COOCH.sub.2 A6* 94a SC.sub.2 H.sub.5 SC.sub.2 H.sub.5 CHCH C.sub.6 H.sub.5 95a SC.sub.2 H.sub.5 SC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 96a SC.sub.2 H.sub.5 SC.sub.2 H.sub.5 CH.sub.2 O C.sub.6 H.sub.5 97a SC.sub.2 H.sub.5 SC.sub.2 H.sub.5 OCH.sub.2 C.sub.6 H.sub.5 98a SC.sub.2 H.sub.5 SC.sub.2 H.sub.5 SCH.sub.2 C.sub.6 H.sub.5 99a SC.sub.2 H.sub.5 SC.sub.2 H.sub.5 O C.sub.6 H.sub.5100a SC.sub.2 H.sub.5 SC.sub.2 H.sub.5 COOCH.sub.2 C.sub.6 H.sub.5101a SC.sub.2 H.sub.5 SC.sub.2 H.sub.5 COOCH.sub.2 1-methylcyclopropyl102a CF.sub.3 CF.sub.3 CHCH C.sub.6 H.sub.5103a CF.sub.3 CF.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5104a CF.sub.3 CF.sub.3 CH.sub.2 O C.sub.6 H.sub.5105a CF.sub.3 CF.sub.3 OCH.sub.2 C.sub.6 H.sub.5106a CF.sub.3 CF.sub.3 SCH.sub.2 C.sub.6 H.sub.5107a CF.sub.3 CF.sub.3 O C.sub.6 H.sub.5108a CF.sub.3 CF.sub.3 COOCH.sub.2 C.sub.6 H.sub.5109a CF.sub.3 CF.sub.3 COOCH.sub.2 1-methylcylopropyl110a CH.sub.3 C.sub.2 H.sub.5 CHCH C.sub.6 H.sub.5111a C.sub.2 H.sub.5 CH.sub.3 CHCH C.sub.6 H.sub.5112a CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5113a C.sub.2 H.sub.5 CH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5114a CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 O C.sub.6 H.sub.5115a C.sub.2 H.sub.5 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5116a CH.sub.3 C.sub.2 H.sub.5 OCH.sub.2 C.sub.6 H.sub.5117a C.sub.2 H.sub.5 CH.sub.3 OCH.sub.2 C.sub.6 H.sub.5118a CH.sub.3 C.sub.2 H.sub.5 COOCH.sub.2 C.sub.6 H.sub.5119a C.sub.2 H.sub.5 CH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5120a CH.sub.3 C.sub.2 H.sub.5 COOCH.sub.2 1-methylcyclopropyl121a C.sub.2 H.sub.5 CH.sub.3 COOCH.sub.2 1-methylcyclopropyl122a CH.sub.3 n-C.sub.3 H.sub.7 CHCH C.sub.6 H.sub.5123a n-C.sub.3 H.sub.7 CH.sub.3 CHCH C.sub.6 H.sub.5124a CH.sub.3 n-C.sub.3 H.sub.7 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5125a n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5126a CH.sub.3 n-C.sub.3 H.sub.7 CH.sub.2 O C.sub.6 H.sub.5127a n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5138a CH.sub.3 n-C.sub.3 H.sub.7 OCH.sub.2 C.sub.6 H.sub.5129a n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.2 C.sub.6 H.sub.5130a CH.sub.3 n-C.sub.3 H.sub.7 COOCH.sub.2 C.sub.6 H.sub.5131a n-C.sub.3 H.sub.7 CH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5132a CH.sub.3 n-C.sub.3 H.sub.7 COOCH.sub.2 1-methylcyclopropyl133a n-C.sub.3 H.sub.7 CH.sub.3 COOCH.sub.2 1-methylcyclopropyl134a CH.sub.3 i-C.sub.3 H.sub.7 CHCH C.sub.6 H.sub.5135a i-C.sub.3 H.sub. 7 CH.sub.3 CHCH C.sub.6 H.sub.5136a CH.sub.3 i-C.sub.3 H.sub.7 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5137a i-C.sub.3 H.sub.7 CH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5138a CH.sub.3 i-C.sub.3 H.sub.7 CH.sub.2 O C.sub.6 H.sub.5139a i-C.sub.3 H.sub.7 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5140a CH.sub.3 i-C.sub.3 H.sub.7 OCH.sub.2 C.sub.6 H.sub.5141a i-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.2 C.sub.6 H.sub.5142a CH.sub.3 i-C.sub.3 H.sub.7 COOCH.sub.2 C.sub.6 H.sub.5143a i-C.sub.3 H.sub.7 CH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5144a CH.sub.3 i-C.sub.3 H.sub.7 COOCH.sub.2 1-methylcyclopropyl145a i-C.sub.3 H.sub.7 CH.sub.3 COOCH.sub.2 1-methylcyclopropyl146a CH.sub.3 OCH.sub.3 CHCH C.sub.6 H.sub.5147a OCH.sub.3 CH.sub.3 CHCH C.sub.6 H.sub.5148a CH.sub.3 OCH.sub.3 CH.sub.2 CH.sub. 2 C.sub.6 H.sub.5149a OCH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5150a CH.sub.3 OCH.sub.3 CH.sub.2 O C.sub.6 H.sub.5151a OCH.sub.3 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5152a CH.sub.3 OCH.sub.3 OCH.sub.2 C.sub.6 H.sub.5153a OCH.sub.3 CH.sub.3 OCH.sub.2 C.sub.6 H.sub.5154a CH.sub.3 OCH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5155a OCH.sub.3 CH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5156a CH.sub.3 OCH.sub.3 COOCH.sub.2 1-methylcyclopropyl157a OCH.sub.3 CH.sub.3 COOCH.sub.2 1-methylcyclopropyl158a C.sub.2 H.sub.5 OCH.sub.3 CHCH C.sub.6 H.sub.5159a OCH.sub.3 C.sub.2 H.sub.5 CHCH C.sub.6 H.sub.5160a C.sub.2 H.sub.5 OCH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5161a OCH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5162a C.sub.2 H.sub.5 OCH.sub.3 CH.sub.2 O C.sub.6 H.sub.5163a OCH.sub.3 C.sub.2 H.sub.5 CH.sub.2 O C.sub.6 H.sub.5164a C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.2 C.sub.6 H.sub.5165a OCH.sub.3 C.sub.2 H.sub.5 OCH.sub.2 C.sub.6 H.sub.5166a C.sub.2 H.sub.5 OCH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5167a OCH.sub.3 C.sub.2 H.sub.5 COOCH.sub.2 C.sub.6 H.sub.5168a C.sub.2 H.sub.5 OCH.sub.3 COOCH.sub.2 1-methylcyclopropyl169a OCH.sub.3 C.sub.2 H.sub.5 COOCH.sub.2 1-methylcyclopropyl170a CH.sub.3 SCH.sub.3 CHCH C.sub.6 H.sub.5171a SCH.sub.3 CH.sub.3 CHCH C.sub.6 H.sub.5172a CH.sub.3 SCH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5173a SCH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5174a CH.sub.3 SCH.sub.3 CH.sub.2 O C.sub.6 H.sub.5175a SCH.sub.3 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5176a CH.sub.3 SCH.sub.3 OCH.sub. 2 C.sub.6 H.sub.5177a SCH.sub.3 CH.sub.3 OCH.sub.2 C.sub.6 H.sub.5178a CH.sub.3 SCH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5179a SCH.sub.3 CH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5180a CH.sub.3 SCH.sub.3 COOCH.sub.2 1-methylcyclopropyl181a SCH.sub.3 CH.sub.3 COOCH.sub.2 1-methylcyclopropyl182a C.sub.2 H.sub.5 SCH.sub.3 CHCH C.sub.6 H.sub.5183a SCH.sub.3 C.sub.2 H.sub.5 CHCH C.sub.6 H.sub.5184a C.sub.2 H.sub.5 SCH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5185a SCH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5186a C.sub.2 H.sub.5 SCH.sub.3 CH.sub.2 O C.sub.6 H.sub.5187a SCH.sub.3 C.sub.2 H.sub.5 CH.sub.2 O C.sub.6 H.sub.5188a C.sub.2 H.sub.5 SCH.sub.3 OCH.sub.2 C.sub.6 H.sub.5189a SCH.sub.3 C.sub.2 H.sub.5 OCH.sub.3 C.sub.6 H.sub.5190a C.sub.2 H.sub.5 SCH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5191a SCH.sub.3 C.sub.2 H.sub.5 COOCH.sub.2 C.sub.6 H.sub.5192a C.sub.2 H.sub.5 SCH.sub.3 COOCH.sub.2 1-methylcyclopropyl193a SCH.sub.3 C.sub.2 H.sub.5 COOCH.sub.2 1-methylcyclopropyl194a CH.sub.3 ##STR14## CHCH C.sub.6 H.sub.5195a ##STR15## CH.sub.3 CHCH C.sub.6 H.sub.5196a CH.sub.3 ##STR16## CH.sub.2 CH.sub.2 C.sub.6 H.sub.5197a ##STR17## CH.sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5198a CH.sub.3 ##STR18## CH.sub.2 O C.sub.6 H.sub.5199a ##STR19## CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5200a CH.sub. 3 ##STR20## OCH.sub.2 C.sub.6 H.sub.5201a ##STR21## CH.sub.3 OCH.sub.2 C.sub.6 H.sub.5202a CH.sub.3 ##STR22## COOCH.sub.2 C.sub.6 H.sub.5203a ##STR23## CH.sub.3 COOCH.sub.2 C.sub.6 H.sub.5204a CH.sub.3 ##STR24## COOCH.sub.2 1-methylcyclopropyl205a ##STR25## CH.sub.3 COOCH.sub.2 1-methylcyclopropyl__________________________________________________________________________
TABLE 3__________________________________________________________________________ ##STR26##No. R.sup.1 R.sup.2 Y Z Data__________________________________________________________________________ 1b (CH.sub.2).sub.3 CHCH C.sub.6 H.sub.5 2b (CH.sub.2).sub.3 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 3b (CH.sub.2).sub.3 CH.sub.2 O C.sub.6 H.sub.5 4b (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 5b (CH.sub.2).sub.3 COOCH.sub.2 C.sub.6 H.sub.5 6b (CH.sub.3).sub.3 COOCH.sub.2 1-methylcyclopropyl 7b (CH.sub.2).sub.4 CHCH C.sub.6 H.sub.5 8b (CH.sub.2).sub.4 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 9b (CH.sub.2 ).sub.4 CH.sub.2 O C.sub.6 H.sub.510b (CH.sub.2).sub.4 OCH.sub.2 C.sub.6 H.sub.511b (CH.sub.2).sub.4 COOCH.sub.2 C.sub.6 H.sub.512b (CH.sub.2).sub.4 COOCH.sub.2 1-methylcyclopropyl13b (CH.sub.2).sub.5 CHCH C.sub.6 H.sub.514b (CH.sub.2).sub.5 CH.sub.2 CH.sub.2 C.sub.6 H.sub.515b (CH.sub.2).sub.5 CH.sub.2 O C.sub.6 H.sub.516b (CH.sub.2).sub.5 OCH.sub.2 C.sub.6 H.sub.517b (CH.sub.2).sub.5 COOCH.sub.2 C.sub.6 H.sub.518b (CH.sub.2).sub.5 COOCH.sub.2 1-methylcyclopropyl19b CHCHCHCH CHCH C.sub.6 H.sub.520b CHCHCHCH CH.sub.2 CH.sub.2 C.sub.6 H.sub.521b CHCHCHCH CH.sub.2 O C.sub.6 H.sub.522b CHCH CHCH OCH.sub.2 C.sub.6 H.sub.523b CHCHCHCH COOCH.sub.2 C.sub.6 H.sub.524b CHCHCHCH COOCH.sub.2 1-methylcyclopropyl25b CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CHCH C.sub.6 H.sub.526b CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.527b CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 O C.sub.6 H.sub.528b CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.529b CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 COOCH.sub.2 C.sub.6 H.sub.530b CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 COOCH.sub.2 1-methylcyclopropyl31b OCH.sub.2 CH.sub.2 O CHCH C.sub.6 H.sub.532b OCH.sub.2 CH.sub.2 O CH.sub.2 CH.sub.2 C.sub.6 H.sub.533b OCH.sub.2 CH.sub.2 O CH.sub. 2 O C.sub.6 H.sub.534b OCH.sub.2 CH.sub.2 O OCH.sub.2 C.sub.6 H.sub.535b OCH.sub.2 CH.sub.2 O COOCH.sub.2 C.sub.6 H.sub.536b OCH.sub.2 CH.sub.2 O COOCH.sub.2 1-methylcyclopropyl37b (CH.sub.2).sub.3 O CHCH C.sub.6 H.sub.538b (CH.sub.2).sub.3 O CH.sub.2 CH.sub.2 C.sub.6 H.sub.539b (CH.sub.2).sub.3 O CH.sub.2 O C.sub.6 H.sub.540b (CH.sub.2).sub.3 O OCH.sub.2 C.sub.6 H.sub.541b (CH.sub.2).sub.3 O COOCH.sub.2 C.sub.6 H.sub.542b (CH.sub.2).sub.3 O COOCH.sub.2 1-methylcyclopropyl43b SCH.sub.2 CH.sub.2 S CHCH C.sub.6 H.sub.544b SCH.sub.2 CH.sub.2 S CH.sub.2 CH.sub.2 C.sub.6 H.sub.545b SCH.sub.2 CH.sub.2 S CH.sub.2 O C.sub. 6 H.sub.546b SCH.sub.2 CH.sub.2 S OCH.sub.2 C.sub.6 H.sub.547b SCH.sub.2 CH.sub.2 S COOCH.sub.2 C.sub.6 H.sub.548b SCH.sub.2 CH.sub.2 S COOCH.sub.2 1-methylcyclopropyl49b S(CH.sub.2).sub.3 S CHCH C.sub.6 H.sub.550b S(CH.sub.2).sub.3 S CH.sub.2 CH.sub.2 C.sub.6 H.sub.551b S(CH.sub.2).sub.3 S CH.sub.2 O C.sub.6 H.sub.552b S(CH.sub.2).sub.3 S OCH.sub.2 C.sub.6 H.sub.553b S(CH.sub.2).sub.3 S COOCH.sub.2 C.sub.6 H.sub.554b S(CH.sub.2).sub.3 S COOCH.sub.2 1-methylcyclopropyl55b CH.sub.2 OCH.sub.2 CH.sub.2 CHCH C.sub.6 H.sub.556b CH.sub.2 CH.sub.2 OCH.sub.2 CHCH C.sub.6 H.sub.557b CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub. 558b CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.559b CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 O C.sub.6 H.sub.560b CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 O C.sub.6 H.sub.561b CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.562b CH.sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C.sub.6 H.sub.563b CH.sub.2 OCH.sub.2 CH.sub.2 COOCH.sub.2 C.sub.6 H.sub.564b CH.sub.2 CH.sub.2 OCH.sub.2 COOCH.sub.2 C.sub.6 H.sub.565b CH.sub.2 OCH.sub.2 CH.sub.2 COOCH.sub.2 1-methylcyclopropyl66b CH.sub.2 CH.sub.2 OCH.sub.2 COOCH.sub.2 1-methylcyclopropyl67b COOCH.sub.2 CH.sub.2 CHCH C.sub.6 H.sub.568b CH.sub.2 CH.sub.2 OCO CHCH C.sub.6 H.sub.569b COOCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.570b CH.sub.2 CH.sub.2 OCO CH.sub.2 CH.sub.2 C.sub.6 H.sub.571b COOCH.sub.2 CH.sub.2 CH.sub.2 O C.sub.6 H.sub.572b CH.sub.2 CH.sub.2 OCO CH.sub.2 O C.sub.6 H.sub.573b COOCH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.574b CH.sub.2 CH.sub.2 OCO OCH.sub.2 C.sub.6 H.sub.575b COOCH.sub.2 CH.sub.2 COOCH.sub.2 C.sub.6 H.sub.576b CH.sub.2 CH.sub.2 OCO COOCH.sub.2 C.sub.6 H.sub.577b COOCH.sub.2 CH.sub.2 COOCH.sub.2 1-methylcyclopropyl78b CH.sub.2 CH.sub.2 OCO COOCH.sub.2 1-methylcyclopropyl__________________________________________________________________________
In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the Ascomycetes and Basidiomycetes classes. Some of them have a systemic action and can be used as foliar and soil fungicides.
The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.
The novel compounds are particularly useful for controlling the following plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits.
Podosphaera leucotricha in apples,
Uncinula necator in vines,
Puccinia species in cereals,
Rhizoctonia species in cotton and lawns,
Ustilago species in cereals and sugarcane,
Venturia inaequalis (scab) in apples,
Helminthosporium species in cereals,
Septoria nodorum in wheat,
Botrytis cinerea (gray mold) in strawberries and grapes,
Cercospora arachidicola in groundnuts,
Pseudocercosporella herpotrichoides in wheat and barley,
Pyricularia oryzae in rice,
Phytophthora infestans in potatoes and tomatoes,
Fusarium and Verticillium species in various plants,
Plasmopara viticola in grapes,
Alternaria species in fruit and vegetables.
The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi.
The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene, chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions, alcohols (e.g., methanol, butanol, ketones (e.g., cyclohexanone, amines e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals e.g., highly disperse silica and silicates); 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 liquors and methylcellulose.
The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, e.g.. against Paecilomyces variotii.
The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.
Examples of formulations are given below.
I. 90 parts by weight of compound no. 151 (Table 1) is mixed with 10 parts by weight of N-methyl-.alpha.-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.
II. 20 parts by weight of compound no. 151 (Table 1) is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.
III. 20 parts by weight of compound no. 151 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.
IV. 20 parts by weight of compound no. 151 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210.degree. and 280.degree. C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.
V. 80 parts by weight of compound no. 151 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-.alpha.-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfate waste liquor, and 7 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in water, a spray liquor is obtained.
VI. 3 parts by weight of compound no. 151 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.
VII. 30 parts by weight of compound no. 151 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.
VIII. 40 parts by weight of compound no. 151 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in water gives an aqueous dispersion.
IX. 20 parts by weight of compound no. 151 is intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in an increase in the fungicidal spectrum.
The following list of fungicides with which the novel compounds may be combined is intended to illustrate possible combinations but not to impose any restrictions.
Examples of fungicides which may be combined with the novel compounds are:
sulfur,
dithiocarbamates and their derivatives, such as
ferric dimethyldithiocarbamate,
zinc dimethyldithiocarbamate,
zinc ethylenebisdithiocarbamate,
manganese ethylenebisdithiocarbamate,
manganese zinc ethylenediaminebisdithiocarbamate,
tetramethylthiuram disulfides,
ammonia complex of zinc N,N'-ethylenebisdithiocarbamate,
ammonia complex of zinc N,N'-propylenebisdithiocarbamate.
zinc N,N'-propylenebisdithiocarbamate and
N,N'-polypropylenebis(thiocarbamyl) 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 and
diisopropyl 5-nitroisophthalate;
heterocyclic substances, such as
2-heptadecylimidazol-2-yl acetate,
2,4-dichloro-6-(o-chloroanilino)-s-triazine,
O,O-diethyl phthalimidophosphonothioate,
5-amino-l-1[-bis-(dimethylamino)]-3-phosphinyl-1,2,4-troiazole,
2,3-dicyano-1,4-dithioanthraquinone,
2-thio-1,3-dithio[4,5-b]quinoxaline,
methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate,
2-methoxycarbonylaminobenzimidazole,
2-fur-2-yl-benzimidazole,
2-thiazol-4-yl)benzimidazole,
N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide.
N-trichloromethylthiotetrahydrophthalimide,
N-trichloromethylthiophthalimide,
N-dichlorofluoromethylthlo-N',N'-dimethyl-N-phenylsulfuric acid diamide,
5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,
2-thiocyanatomethylthlobenzothiazole.
1,4-dichloro-2,5-dimethoxybenzene,
4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone.
2-thiopyridine 1-oxide.
8-hydroxyquinoline and its copper salt.
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne 4,4-dioxide,
2-methylfuran-3-carboxanilide.
2,5-dimethylfuran-3-carboxanilide,
2,4,5-trimethylfuran-3-carboxanilide,
2,5-dimethyl-N-cyclohexylfuran-3-carboxamide,
N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboxamide,
2-methylbenzanilide,
2-iodobenzanilide,
N-formyl-N-morpholine-2,2,2-trichloroethylacetal,
piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl-formamide),
1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane.
2,6-dimethyl-N-tridecylmorpholine and its salts,
2,6-dimethyl-N-cyclododecylmorpholine and its salts,
N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-dmethylmorpholine,
N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-piperidine.
1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole
1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,
N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolyl-urea,
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one.
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol,
1-(4-phenylphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,
.alpha.-(2-chlorophenyl)-.alpha.(4-chlorophenyl)-5-pyrimidinemethanol,
5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimidine,
bis-(p-chlorophenyl)-3-pyridinemethanol,
1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene.
1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene,
and various fungicides, such as dodecylguanidine acetate,
3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide,
hexachlorobenzene,
DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate,
methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate,
N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactone,
methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate,
5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,
3-[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,
3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin,
N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,
2-cyano-[N-ethylaminocarbonyl)-2-methoximino]-acetamide,
1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole,
2,4-difluoro-.alpha.-(1H-1,2,4-triazole-1-ylmethyl)-benzhydryl alcohol,
N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, and
1-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-1H-1,2,4-triazole.
Use example
For comparison purposes, N-tridecyl-2,6-dimethylmorpholine (A) disclosed in DE 1,164,152 was used.
Use example
Action on Pyricularia oryzae (protective)
Leaves of potted rice seedlings of the "Bahia" variety were sprayed to runoff with aqueous emulsions consisting (dry basis) of 80% of active ingredient and 20% of emulsifier, and inoculated 24 hours later with an aqueous spore suspension of Pyricularia oryzae. The plants were then set up in climatic cabinets at 22.degree. to 24.degree. C. and a relative humidity of 95 to 99%. The spread of the disease was determined after 6 days.
The results show that active ingredient 151 (Table 1) has, when applied as a 0.05wt % spray liquor, a better fungicidal action (80%) than prior art comparative agent A (40%).
Claims
  • 1. Acrylates of the formula I ##STR27## wherein R.sup.1 and R.sup.2 are halogen or C.sub.1-4 -alkyl, C.sub.1-3 -alkoxy or C.sub.1-3 -alkylthio, where alkyl is unsubstituted or substituted by halogen, hydroxy, C.sub.1-3 -alkoxy, C.sub.1-3 -haloalkyl or C.sub.1-3 -haloalkoxy;
  • X is hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halo-C.sub.1 -C.sub.4 -alkyl;
  • n is 1, 2, 3 or 4;
  • y is C.sub.1 -C.sub.4 -alkylene, C.sub.2 -C.sub.4 -alkenylene, C.sub.2 -C.sub.4 -alkynylene, O, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted N, oxy-C.sub.1 -C.sub.4 -alkylene, thio-C.sub.1 -C.sub.4 -alkylene, --NCOO--, methyleneoxy or methylenethio; and
  • Z is hydrogen, alkyl, cycloalkyl, aryl, aralkyl, aralkenyl, aralkoxy, aryloxy, aryloxyalkyl, alkoxy, alkoxyalkyl, alkylthio, or haloalkyl, these radicals being unsubstituted or substituted by halogen, cyano, nitro, alkyl, alkenyl, haloalkenyl, alkoxy, haloalkyl, alkoxycarbonyl or phenyl;
  • with the proviso that R.sup.1 and R.sup.2 cannot both be methyl, when X is hydrogen, Y is methylene, and Z is hydrogen, simultaneously.
  • 2. A compound of the formula I as set forth in claim 1, where R.sup.1 is methyl, R.sup.2 is methyl, y is --CH.sub.2 O-- and Z is 2--CH.sub.3 --C.sub.6 H.sub.4.
  • 3. A process for combating fungi, wherein the fungi, or the materials, plants, seed or the soil to be protected against fungus attack are treated with a fungicidally effective amount of a compound of the formula I ##STR28## wherein R.sup.1 and R.sup.2 are halogen or C.sub.1-4 -alkyl, C.sub.1-3 -alkoxy or C.sub.1-3 -alkylthio, where alkyl is unsubstituted or substituted by halogen, hydroxy, C.sub.1-3 -alkoxy, C.sub.1-3 -haloalkyl or C.sub.1-3 -haloalkoxy;
  • X is hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halo-C.sub.1 -C.sub.4 alkyl;
  • n is 1, 2, 3 or 4;
  • Y is C.sub.1 -C.sub.4 -alkylene, C.sub.2 -C.sub.4 -alkenylene, C.sub.2 -C.sub.4 -alkynylene, O, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted N, oxy-C.sub.1 -C.sub.4 -alkylene, thio-C.sub.1 -C.sub.4 -alkylene, --NCOO--, methyleneoxy or methylenethio; and
  • Z is hydrogen, alkyl, cycloalkyl, aryl, aralkyl, aralkenyl, aralkoxy, aryloxy, aryloxyalkyl, alkoxy, alkoxyalkyl, alkylthio, or haloalkyl, these radicals being unsubstituted or substituted by halogen, cyano, nitro, alkyl, alkenyl, haloalkenyl, alkoxy, haloalkyl, alkoxycarbonyl or phenyl.
  • 4. A fungicide containing an inert carrier and a fungicidally effective amount of a compound of the formula I ##STR29## wherein R.sup.1 and R.sup.2 are halogen or C.sub.1-4 -alkyl, C.sub.1-3 -alkoxy or C.sub.1-3 -alkylthio, where alkyl is unsubstituted or substituted by halogen, hydroxy, C.sub.1-3 -alkoxy, C.sub.1-3 -haloalkyl, or C.sub.1-3 -haloalkoxy;
  • X is hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halo-C.sub.1 -C.sub.4 -alkyl;
  • n is 1, 2, 3 or 4;
  • y is C.sub.1 -C.sub.4 -alkylene, C.sub.2 -C.sub.4 -alkenylene, C.sub.2 -C.sub.4 -alkynylene, O, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted N, oxy-C.sub.1 -C.sub.4 -alkylene, thio-C.sub.1 -C.sub.4 -alkylene, --NCOO--, methyleneoxy or methylenethio; and
  • Z is hydrogen, alkyl, cycloalkyl, aryl, aralkyl, aralkenyl, aralkoxy, aryloxy, aryloxyalkyl, alkoxy, alkoxyalkyl, alkylthio, or haloalkyl, these radicals being unsubstituted or substituted by halogen, cyano, nitro, alkyl, alkenyl, haloalkenyl, alkoxy, haloalkyl, alkoxycarbonyl or phenyl.
Priority Claims (1)
Number Date Country Kind
3816577 May 1988 DEX
US Referenced Citations (7)
Number Name Date Kind
3622569 Lemieux Nov 1971
4178460 Berkelhammer et al. Dec 1979
4199595 Berkelhammer et al. Apr 1980
4239777 Berkelhammer et al. Dec 1980
4709078 Schriner et al. May 1986
4723034 Schriner et al. May 1986
4782177 Lausberg Feb 1987
Foreign Referenced Citations (2)
Number Date Country
178826 Apr 1986 EPX
260832 Mar 1988 EPX
Non-Patent Literature Citations (5)
Entry
CA 112(7) 55007n, 1989.
CA 90(23):186606p, 1979.
CA 106(7) 50525, 1986.
Chemical Abstracts, vol. 95, #168044c (1981).
Journal of Organic Chemistry, vol. 53, pp. 607-610 (1988).