.alpha.-arylacrylates and fungicides containing these compounds

The present invention relates to novel .alpha.-arylacrylates, their preparation and their use as fungicides.
Methyl .alpha.-phenylacrylate is known (C.A. Reg. No. 1865-29-8).
We have found that novel .alpha.-arylacrylate derivatives of the formula I ##STR2## where Y is unsubstituted or substituted C.sub.1 -C.sub.4 -alkylene, unsubstituted or substituted C.sub.2 -C.sub.4 -alkenylene, C.sub.2 -C.sub.4 -alkynylene, O,S(O).sub.m (m=0, 1 or 2), unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted N, oxycarbonyl, carbonyloxy, C.sub.1 -C.sub.10 -oxycarbonylalkylene, C.sub.1 -C.sub.10 -carbonyloxyalkylene, C.sub.2 -C.sub.10 -oxyalkyleneoxy, C.sub.1 -C.sub.10 -oxyalkylene, C.sub.1 -C.sub.10 -alkyleneoxy, C.sub.1 -C.sub.10 -thioalkylene, azo, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted carbonylamino, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted aminocarbonyl or unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted aminocarbonyloxy and
Z is hydrogen, halogen, C.sub.1 -C.sub.18 -alkyl, C.sub.2 -C.sub.18 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.2 -C.sub.4 -alkynyl, aryl, aryl-C.sub.1 -C.sub.10 -alkyl, aryl-C.sub.2 -C.sub.10 -alkenyl, aryloxy, aryloxy-C.sub.1 -C.sub.10 -alkyl, alkoxy-C.sub.1 -C.sub.10 -alkyl, halo-C.sub.1 -C.sub.10 -alkyl, aryloxy-C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, which are unsubstituted or substituted by halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.2 -C.sub.4 -haloalkenyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, unsubstituted or substituted phenyl or unsubstituted or substituted phenoxy, or is C-bonded, unsubstituted or substituted 5-membered heterocyclic structure which contains one to four indentical or different heteroatoms, i.e. nitrogen, oxygen or sulfur in that two adjacent substituents may form an aromatic or heteroaromatic ring which may be bonded to an ethylene unit, have a very good fungicidal action which is better than that of the known fungicides.
Y is preferably methylene, ethylene, ethenylene, ethynylene, O, S, methyleneoxy, ethyleneoxy, oxymethylene, thiomethylene, carbonyloxy, oxycarbonyl, carbonyloxymethylene or --HN--CO--O--.
Z is preferably hydrogen, halogen (e.g. fluorine, chlorine or bromine), C.sub.1 -C.sub.18 -alkyl, (e.g. methyl, ethyl, n-or isopropyl, n-, sec-, iso- or tert-butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,1-dimethylpropyl, 3-hexyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-pentadecyl, n-heptadecyl or 2,6-dimethylhept-1-yl), cyanomethyl, C.sub.2 -C.sub.9 -alkenyl (e.g. vinyl, prop-2-en-2-yl, prop-1-en-1-yl, but-2-en-2-yl, 2-methylprop-1-en-1-yl, allyl, but-2-en-1-yl, 3-methylbut-2-en-1yl, penta-1,3-dien-1-yl, 2,6-dimethylhepta-1,5-dien-1-yl or 2,6-dimethylhept-5-en-1-yl); C.sub.2 -alkynyl (e.g. ethynyl or 2-phenylethynyl), C.sub.1 - or C.sub.2 -alkoxy-C.sub.1 - or -C.sub.2 -alkyl (methoxymethyl, ethoxymethyl or 1-methoxyethyl), C.sub.3 -C.sub.6 -cycloalkyl (e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or 1-methylcyclopropyl), and the following substituted cyclopropyl radicals being examples:
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)
2-carbomethoxycyclopropyl (A11)
or halo-C.sub.1 - or C.sub.2 -alkyl (e.g. chloromethyl, 1-chloroethyl, dichloromethyl, trichloromethyl, bromomethyl or trifluoromethyl), phenyl, substituted phenyl, such as halophenyl (e.g. 2-fluoro, 3-fluoro-, 4-fluoro-, 6-fluoro-, 2-chloro-, 2,4-difluoro-, 2,6-difluoro, 2,3,4,5,6-pentafluoro-, 3-chloro-, 4-chloro-, 2,4-dichloro-, 2,5-dichloro-, 2,6-dichloro-, 3,4-dichloro-, 3,5-dichloro-, 2,4,5-trichloro-, 2,3,4,5,6-pentachloro-, 2-bromo-, 3-bromo-, or 4-bromophenyl);
C.sub.1 -C.sub.4 -alkylphenyl (e.g. 2-methyl-, 3-methyl-, 4-methyl-, 2,3-dimethyl-, 2,4-dimethyl-, 2,5-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl-, 3,5-dimethyl-, 2,4,6-trimethyl-or 4-tert-butylphenyl); arylphenyl (e.g. 2-phenyl- or 4-phenylphenyl); halo-C.sub.1 -alkylphenyl (e.g. 2-trifluoro-, 3-trifluoro-or 4-trifluoromethylphenyl); C.sub.1 -C.sub.4 -alkoxyphenyl (e.g. 2-methoxy-, 3-methoxy-, 4-methoxy-, 3,4-dimethoxy-, 3,4,5-trimethoxy- or 4-tert-butoxyphenyl); 2-, 3- or 4-phenoxyphenyl;
Substituted benzyl (e.g. halobenzyl, such as 2-fluoro-, 3-fluoro-, 4-fluoro-, 2-chloro-, 3-chloro-, 4-chloro-, 2-chloro-, 6-fluoro-, 2,4-dichloro-, 2,6-dichloro-, 3,5-dichloro-, 2,4,6-trichloro-, 2-bromo-, 3-bromo-, 4-bromo-, 2-methyl-, 3-methyl-, 4-methyl-, 4-tert-butyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2,4,6-trimethyl-, 2-methoxy-, 3-methoxy-, 4-methoxy-, 2-trifluoromethyl-, 3-trifluoromethyl-, 4-trifluoromethyl-, 4-tert-butoxy-, 4-phenoxy-or 4-phenylbenzyl, .alpha.-methyl-.alpha.-ethyl-, .alpha.-isopropyl-, .alpha.-hydroxy-, 2-methoxy-.alpha.-hydroxy-, 4-methoxy-.alpha.-hydroxy-, 3,4-dimethoxy-.alpha.-hydroxy-, 2-methoxy-.alpha.-methoxy-, 4-methoxy-.alpha.-methoxy- or 3,4-dimethoxy-.alpha.-methoxybenzyl); unsubstituted or substituted phenethyl (e.g. phenyl-, 1-methyl-2-phenyl-, 2-(para-tert-butylphenyl)-, 2-(para-tert-butylphenyl)-1-methyl-, 2-(ortho-chlorophenyl)-, 2-(meta-chlorophenyl)- or 2-(para-chlorophenyl)ethyl); unsubstituted or substituted or styryl (e.g. styryl or 2'-chloro-, 3'-chloro-, 4'-chloro-, 2',4'-dichloro-, 2'-fluoro, 4'-fluoro-, 2'-methyl-, 4' -methyl-, 4'-tert-butyl-, 2'-methoxy-, 4'-methoxy- or 4'-phenoxystyryl); phenyl-C.sub.3 -C.sub.6 -alkyl (e.g. 3-phenylpropyl, 2-methyl-3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 6-phenylhexyl or 3-(4'-tert-butylphenyl)-2-methylpropyl);
aryloxy, such as substituted phenoxy (e.g. 2-chloro-, 3-chloro-, 4-chloro-, 2-methyl-, 4-methyl-, 2-methoxy-, 4-methoxy-, 2-trifluoromethyl- or 4-trifluoromethylphenoxy); aryloxy-C.sub.1 -C.sub.6 -alkyl, such as unsubstituted or substituted phenoxymethyl (e.g. 2-chloro-, 4-chloro-, 2-methyl-, 4-methyl-, 2-methoxy-, 4-methoxy- or 4-tert-butylphenoxymethyl); unsubstituted or substituted phenoxyethyl (e.g. 2-chloro-, 4-chloro-, 4-fluoro-, 2-methyl-, 4-methyl-, 2-methoxy-, 4-methoxy- or 4-tert-butylphenoxyethyl), unsubstituted or substituted C.sub.3 -C.sub.6 -phenoxyalkyl (e.g. phenoxypropyl, 3-(ortho-chlorophenoxy)-propyl, 3-(para-chlorophenoxy)-propyl, 4-phenoxybutyl, 4-(ortho-chlorophenoxy)-butyl, 4-(para-chlorophenoxy)-butyl, 5-phenoxypentyl, 5-(ortho-chlorophenoxy)-pentyl, 5-(para-chlorophenoxy)-pentyl or 6-phenoxyhexyl); phenoxyethoxy; methoxycarbonyl or tert-butoxycarbonyl; unsubstituted or substituted hetaryl (e.g. furyl, 2-furyl, 3-furyl, 5-nitro-2- and -3-furyl, 5-chloro-2- and -3-furyl, benzofuran-2- and -3-yl, thienyl, 2-thienyl, 3-thienyl, 5-nitro-2- and -3-thienyl, 5-chloro- 2-and -3-thienyl and benzothien-2- and -3-yl);
N-methylpyrrol-2- and -3-yl, N-methylpyrazol-3-, -4- and -5-yl, N-methylimidazol-2-, -4- and -5-yl, 1-methyl-1,2,3-triazol-4- and -5-yl, 1-methyl-1,2,4-triazol-3- and -5-yl, 1-methyltetrazol-5-yl, isoxazol-3-, -4- and -5-yl, benzisoxazol-3-yl, benzoxazol-2-yl, oxazol-2-, -4- and -5-yl, thiazol-2-, -4- and -5-yl, benzothiazol-2-yl, benzoisothiazol-3-yl, isothiazol-3-, -4- and -5-yl, 1,2,3-thiadiazol-4-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-3-yl or 1,3-thiazolo[4,5-b]pyridin-2-yl) and substituted hetarylalkenyl (e.g. 2-(2'- and 3'-furyl)-, 2-(5'-nitro-2'- and -3'-furyl)-, 2-(2'- and 3'-thienyl)-and 2-(5'-nitro-2'- and -3'-thienyl)-ethenyl).
The compounds of the formula I can be prepared, for example, by the reactions shown in Scheme 1. ##STR3##
The phenylacetates of the formula II are converted in a conventional manner via the 3-aryl-2-oxosuccinates III into the methyl .alpha.-arylacrylates I (cf. E. Galantay et al., J. Org. Chem. 35 (1970), 4277). For this purpose, the phenylacetate (II) is acylated with a dialkyl oxalate with the aid of a base, e.g. sodium methylate or sodium ethylate, to give the diesters III and the latter are subjected to an addition reaction with formaldehyde. By hydrolysis with an aqueous base, e.g. potassium carbonate, the atropaic acid derivatives I are obtained. The compounds of the formula I can be prepared directly from phenylacetates II with paraformaldehyde, potassium carbonate and a catalytic amount of phase transfer catalyst, e.g. tetrabutylammonium iodide, in, for example, toluene [cf. W. Seitz and A. Michel, DE 3 317 356].
The .alpha.-ketocarboxylates of the formula IV can be converted into the acrylates of the formula I by a Wittig reaction with methylenetriphenylphosphorane in a conventional manner in the presence of a base, e.g. n-butyllithium, potassium tert-butylate, sodium hydride or sodium methylate (cf. G. Wittig and U. Schollkopf, Org. Synth., Coll. Vol. V (1973), 751).
Preparation of the .alpha.-ketoesters of the formula IV is known (EP 178826).
For example, the aromatic Grignard compounds VII are reacted with imidazolidenes of the formula VIII (J. S. Nimitz and H. S. Mosher, J. Org. Chem. 46 (1981), 211), where Y and Z have the abovementioned meanings. ##STR4##
The oxidation of substituted acetophenones (IX) with potassium permanganate in pyridine/water/potassium hydroxide ##STR5## (cf. J. W. F. McOmie and S. D. Thata, J. Chem. Soc. 1965, 5298) gives the phenylketoacids X, which can be esterified with, for example, methyl chloroformate/triethylamine to give the .alpha.-ketoesters IV (cf. J. M. Domagala, Tetrahedron Lett. 21 (1980), 4957).
The benzyl cyanides V can be converted into the .alpha.-arylacrylonitriles of the formula VI by treating them with a base, e.g. sodium methylate, and formaldehyde (cf. J. M. Stewart and C. H. Chang, J. Org. Chem. 21 (1956), 635).
The nitriles VI are converted into the acrylates of the formula I with a methanolic mineral acid, e.g. hydrochloric acid or sulfuric acid (cf. E. N. Zil'berman, Russ. Chem. Rev. 31 (1962), 615).
The Examples which follow illustrate the preparation of the novel compounds of the formula I.

EXAMPLE 1
Preparation of methyl 2-[2'-cinnamoyloxymethyl)-phenyl]acrylate (No. 866)
a) Preparation of methyl ortho-bromomethylphenylglyoxalate
50.0 g (0.28 mole) of methyl ortho-methylphenylglyoxalate are dissolved in 3 liters of carbon tetrachloride, together with 50.0 g (0.28 mole) of freshly crystallized N-bromosuccinimide. The reaction mixture is exposed to a 300 W Hg vapor lamp for one hour and is evaporated down to 1 liter, the organic phase is washed with 3.times.200 ml of water and dried over sodium sulfate, the solvent is distilled off and the residue is chromatographed over silica gel with 1:9 methyl tert-butyl ether/hexane. 10 g of the ketoesters (II, YZ=CH.sub.3) and 21.1 g of the benzyl bromide (II, Y-Z=CH.sub.2 Br) (37%, based on converted ketoester) are obtained as a yellow oil.
.sup.1 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 2-(cinnamoylmethyl)-phenylglyoxalate
10.4 g (56 millimoles) of potassium transcinnamate and 12.0 g (47 millimoles) of methyl orthobromomethylphenylglyoxalate are dissolved in 250 ml of N-methylpyrrolidone, a pinch of potassium iodide is added and the mixture is stirred for 15 hours at room temperature (23.degree. C.). Thereafter, the mixture is poured onto 500 ml of ice water and extracted with 3.times.200 ml of methyl tert-butyl ether and the organic phase is washed with water, dried over sodium sulfate and evaporated down in a rotary evaporator. The yield of ketoester is 15.0 g (99%). Thin layer chromatographic analysis shows that it is virtually pure.
.sup.1 H-NMR (CDCl.sub.3): .delta.=3.97 (s, 3H), 5.62 (s, 2H); 6.55 (d, J=10 Hz; 1H); 7.3-7.85 (m, 9H); 7.77 (d, J=10 Hz, 1H) IR (film): 1728, 1688, 1638, 1210, 1168, 998, 978, 765 cm.sup.-1.
c) Preparation of methyl 2-[2'-(cinnamoyloxymethyl)-phenyl]-acrylate (No. 866)
10.5 g (26 millimoles) of methyltriphenylphosphonium iodide in 100 ml of anhydrous tetrahydrofuran are initially taken under a nitrogen atmosphere. 16.5 ml of a 1.6M solution of n-butyllithium in n-hexane are added dropwise at 0.degree. C. and stirring is continued for 1 hour at 0.degree. C. After the mixture has been cooled to -78.degree. C., 7.5 g (23 millimoles) of the ketoester obtained according to b), in 50 ml of tetrahydrofuran, are slowly added dropwise. The mixture is allowed to reach room temperature and is stirred for a further 12 hours. It is poured into 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 product is obtained by column chromatography over silica gel using 1:9 methyl tert-butyl ether/n-hexane. 2.1 g (28%) of the abovementioned acrylate are obtained as an oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.=3.75 (s, 3H); 5.18 (s, 2H); 5.8 (d, J=1 Hz, 1H); 6.42 (d, J=10 Hz, 1H); 6.60 (d, J=1 Hz, 1H); 7.15-7.60 (m, 9H); 7.68 (d, J=10 Hz; 1H).
IR (film): 1719, 1637, 1311, 1204, 1164, 768 cm.sup.-1.
EXAMPLE 2
Preparation of the Intermediates
Preparation of methyl 2-methylphenylglyoxalate
1.4 g (10 millimoles) of ortho-methylacetophenone, 2.0 g of potassium hydroxide, 200 ml of pyridine and 100 ml of water are initially taken at +10.degree. C. 5 g of potassium permanganate in 250 ml of water are added dropwise and the mixture is stirred for 2 hours at this temperature. Thereafter, sodium bisulfite solution is added dropwise until the red coloration of the mixture vanishes. The mixture is filtered, the filtrate is acidified with concentrated hydrochloric acid and filtered again and this filtrate is extracted with 5.times.50 ml of methyl tert-butyl ether. The organic phase is dried over sodium sulfate and evaporated down and the residue is then directly reacted further (ratio of ketoacid to benzoic acid 8-9:1 according to .sup.1 H-NMR). 2.0 g of the above mixture in 20 ml of dichloromethane are initially taken and 1.6 g (16 millimoles) of triethylamine are added. 1.5 g (16 millimoles) of methyl chloroformate are added dropwise at room temperature. After 1 hour at this temperature, the mixture is extracted with phosphate buffer (pH 7) and evaporation and distillation are carried out.
Bp. 95.degree.-99.degree. C./0.4 mbar; yield: 0.92 g (51%).
IR (film): 1740, 1686, 1602, 1457, 1317, 1285, 1203, 1002, 739 cm.sup.-1.
EXAMPLE 3
Preparation of methyl 2-[2'-(benzyloxyphenyl]-acrylate (No. 446)
25.6 g (0.10 mole) of methyl ortho-benzyloxyphenylacetate, 4.5 g (0.15 mole) of paraformaldehyde, 23.5 g (0.16 mole) of potassium carbonate and 600 mg (2 millimoles) of tetrabutylammonium iodide are added to 50 ml of toluene. The mixture is stirred for 3-4 hours at 80.degree.-85.degree. C., after which it is cooled and 50 ml of water are added. The mixture is shaken, the phases are separated, the aqueous phase is extracted with 2.times.50 ml of toluene and the toluene and the organic phase are extracted with 2.times.50 ml of saturated sodium chloride solution. Drying with Na.sub.2 SO.sub.4 and evaporation give a yellowish oil, which is chromatographed over silica gel using 1:2 methyl tert-butyl ether/hexane. Yield: 16.4 g (61%).
IR (film): 1727, 1602, 1495, 1451, 1276, 1242, 1268, 753, 735, 696 cm.sup.-1.
.sup.1 H-NMR (CDCl.sub.3): .delta.=3.60 (s, 3H); 5.07 (s, 2H); 5.23 (d, J=1 Hz; 1H); 6.26 (d, J=1 Hz; 1H); 6.8-7.0 (m, 2H); 7.1-7.4 (m, 7H).
EXAMPLE 4
Preparation of 2'(2'-methoxycarbonylethen-1'-yl)-benzyltriphenylphosphonium bromide (No. 926)
14 g (80 millimoles) of methyl 2-(2'-methylphenyl)-acrylate, 28.5 g (160 millimoles) of N-bromosuccinimide and 500 ml of carbon tetrachloride are combined and the refluxed mixture is exposed for 3 hours to a mercury vapor lamp (300 W). The mixture is cooled, washed with water, dried with sodium sulfate and then evaporated down. The crude product (methyl 2-(2'-bromomethylphenyl)-acrylate (No. 925)) is dissolved in 500 ml of tetrahydrofuran, 21 g (80 millimoles) of triphenylphosphine are added and the mixture is kept for 15 hours at 23.degree. C. and the boiled for 4 hours at 70.degree. C. The mixture is cooled and filtered under suction, and the residue is washed with methyl tert-butyl ether and dried under reduced pressure to give 16.0 g (39%) of a white powder of melting point 145.degree.-147.degree. C.
.sup.1 H-NMR (CDCl.sub.3 ; No. 925): .delta.=3.78 (s, 3H); 4.42 (s, 2H); 5.90 (d, J=1 Hz; 1H); 6.65 (d, J=1 Hz, 1H); 7.1-7.5 (m, 4H).
.sup.1 H-NMR (CDCl.sub.3 ; No. 926): .delta.=3.62 (s, 3H); 5.07 (sbr, 1H); 5.15 (d, J=1 Hz, 2H); 6.27 (sbr; 1H); 7.0-7.85 (m, 19H).
__________________________________________________________________________No. Z Y Data__________________________________________________________________________1 H CHCH2 CH.sub.3 CHCH3 C.sub.2 H.sub.5 CHCH4 n-C.sub.3 H.sub.7 CHCH5 iso-C.sub.3 H.sub.7 CHCH6 n-C.sub.4 H.sub.9 CHCH7 (CH.sub.3).sub.2 CHCH.sub.2 CHCH8 CH.sub.3 CH.sub.2 CH(CH.sub.3) CHCH9 tert.C.sub.4 H.sub.9 CHCH10 CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 CHCH11 (CH.sub.3).sub.2 CCH.sub.2 CHCH12 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CHCH13 CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5) CHCH14 n-C.sub.5 H.sub.11 CHCH15 n-C.sub.6 H.sub.13 CHCH16 n-C.sub.7 H.sub.15 CHCH17 n-C.sub.8 H.sub.17 CHCH18 n-C.sub.9 H.sub.19 CHCH19 n-C.sub.10 H.sub.21 CHCH20 n-C.sub.15 H.sub.31 CHCH21 n-C.sub.17 H.sub.35 CHCH22 CH.sub.2CH CHCH23 CH.sub.2C(CH.sub.3) CHCH24 CH.sub.3 CHCH CHCH25 CH.sub.3 CHC(CH.sub.3) CHCH26 (CH.sub.3).sub.2 CCH CHCH27 CH.sub.2CHCH.sub.2 CHCH28 CH.sub.3 CHCHCH.sub.2 CHCH29 (CH.sub.3).sub.2 CCHCH.sub.2 CHCH30 CH.sub.3 CHCHCHCH CHCH31 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH CHCH32 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CHCH33 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CHCH34 HCC CHCH35 C.sub.6 H.sub.5CC CHCH36 CH.sub.3 OCH.sub.2 CHCH37 C.sub.2 H.sub.5 OCH.sub.2 CHCH38 CH.sub.3 CH(OCH.sub.3) CHCH39 CNCH.sub.2 CHCH40 cyclopropyl CHCH41 cyclobutyl CHCH42 cyclopentyl CHCH43 cyclohexyl CHCH44 1-methylcyclopropyl CHCH45 2,2-dichloro-1-methyl-cyclopropyl CHCH46 2,2-dichloro-3,3-dimethyl-cyclopropyl CHCH47 2,2,3,3-tetramethylcyclopropyl CHCH48 2-(2'-methyl-1'-propenyl-)-3,3-dimethylcyclopropyl CHCH49 2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl CHCH50 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl CHCH51 2-(2',2'dibromovinyl)-3,3-dimethylcyclopropyl CHCH52 2-phenylcyclopropyl CHCH53 2-(4'-chlorophenyl)cyclopropyl CHCH54 2,2-dichloro-3-phenylcyclopropyl CHCH55 2-carbomethoxy-cyclopropyl CHCH56 ClCH.sub.2 CHCH57 Cl.sub.2 CH CHCH58 Cl.sub.3 C CHCH59 BrCH.sub.2 CHCH60 CF.sub.3 CHCH61 CH.sub.3 CH(Cl) CHCH62 C.sub.6 H.sub.5 (phenyl) CHCH63 2-CH.sub.3C.sub.6 H.sub.4 CHCH64 3-CH.sub.3C.sub.6 H.sub.4 CHCH65 4-CH.sub.3C.sub.6 H.sub.4 CHCH66 2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3 CHCH67 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 CHCH68 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3 CHCH69 3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 CHCH70 3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3 CHCH71 2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2 CHCH72 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 CHCH73 2-C.sub.6 H.sub.5C.sub.6 H.sub.4 CHCH73 2-C.sub.6 H.sub.5C.sub.6 H.sub.4 CHCH74 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 CHCH75 2-ClC.sub.6 H.sub.4 CHCH76 3-ClC.sub.6 H.sub.4 CHCH77 4-ClC.sub.6 H.sub.4 CHCH78 2,4-Cl.sub.2C.sub.6 H.sub. 3 CHCH79 2,5-Cl.sub.2C.sub.6 H.sub.3 CHCH80 2,6-Cl.sub.2C.sub.6 H.sub.3 CHCH81 3,4-Cl.sub.2C.sub.6 H.sub.3 CHCH82 3,5-Cl.sub.2C.sub.6 H.sub.3 CHCH83 2,4,5-Cl.sub.3C.sub.6 H.sub.2 CHCH84 2,3,4,5,6-Cl.sub.5C.sub.6 CHCH85 6-F,2-ClC.sub.6 H.sub.3 CHCH86 2-FC.sub.6 H.sub.4 CHCH87 3-FC.sub.6 H.sub.4 CHCH88 4-FC.sub.6 H.sub.4 CHCH89 2,4-F.sub.2C.sub.6 H.sub.3 CHCH90 2,6-F.sub.2C.sub.6 H.sub.3 CHCH91 2,3,4,5,6-F.sub.5C.sub.6 CHCH92 2-BrC.sub.6 H.sub.4 CHCH93 3-BrC.sub.6 H.sub.4 CHCH94 4-BrC.sub.6 H.sub.4 CHCH95 2-CF.sub.3C.sub.6 H.sub.4 CHCH96 3-CF.sub.3C.sub.6 H.sub.4 CHCH97 4-CF.sub.3C.sub.6 H.sub.4 CHCH98 2-OCH.sub.3C.sub.6 H.sub.4 CHCH99 3-OCH.sub.3C.sub.6 H.sub.4 CHCH100 4-OCH.sub.3C.sub.6 H.sub.4 CHCH101 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3 CHCH102 3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2 CHCH103 4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4 CHCH104 2-phenoxy-C.sub.6 H.sub.4 CHCH105 3-phenoxy-C.sub.6 H.sub.4 CHCH106 4-phenoxy-C.sub.6 H.sub.4 CHCH107 C.sub.6 H.sub.5CH.sub.2 CHCH108 2-FC.sub.6 H.sub.4CH.sub.2 CHCH109 3-FC.sub.6 H.sub.4CH.sub.2 CHCH110 4-FC.sub.6 H.sub.4CH.sub.2 CHCH111 2-ClC.sub.6 H.sub.4CH.sub.2 CHCH112 3-ClC.sub.6 H.sub.4CH.sub.2 CHCH113 4-ClC.sub.6 H.sub.4CH.sub.2 CHCH114 2-Cl, 6FC.sub.6 H.sub.3CH.sub.2 CHCH115 2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CHCH116 2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CHCH117 3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CHCH118 2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2 CHCH119 2-CH.sub.3C.sub.6 H.sub.4CH.sub.2 CHCH120 3-CH.sub.3C.sub.6 H.sub.4CH.sub.2 CHCH121 4-CH.sub.3C.sub.6 H.sub.4CH.sub.2 CHCH122 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CHCH123 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 CHCH124 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 CHCH125 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2 CHCH126 2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CHCH127 3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CHCH128 4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CHCH129 2-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CH CH130 3-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CHCH131 4-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CHCH132 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CHCH133 4-OC.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2 CHCH134 4-C.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2 CHCH135 2-BrC.sub.6 H.sub.4CH.sub.2 CHCH136 3-BrC.sub.6 H.sub.4CH.sub.2 CHCH137 4-BrC.sub.6 H.sub.4CH.sub.2 CHCH138 C.sub.6 H.sub.5CH(CH.sub.3) CHCH139 C.sub.6 H.sub.5CH(C.sub.2 H.sub.5) CHCH140 C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.7) CHCH141 C.sub.6 H.sub.5CH(OH) CHCH142 2-OCH.sub.3C.sub.6 H.sub.4CH(OH) CHCH143 4-OCH.sub.3C.sub.6 H.sub.4CH(OH) CHCH144 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OH) CHCH145 2-OCH.sub. 3C.sub.6 H.sub.4CH(OCH.sub.3) CHCH146 4-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3) CHCH147 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OCH.sub.3) CHCH148 C.sub.6 H.sub.5CH.sub.2 CH.sub.2 CHCH149 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3) CHCH150 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CHCH151 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3) CHCH152 2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CHCH153 3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CHCH154 4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CHCH155 C.sub.6 H.sub.5CHCH CHCH156 2-ClC.sub.6 H.sub.4CHCH CHCH157 3-ClC.sub.6 H.sub.4CHCH CHCH158 4-ClC.sub.6 H.sub.4CHCH CHCH159 2,4-Cl.sub.2C.sub.6 H.sub.3 CHCH CHCH160 2-FC.sub.6 H.sub.4CHCH CHCH161 4-FC.sub.6 H.sub.4CHCH CHCH162 2-CH.sub.3C.sub.6 H.sub.4CHCH CHCH163 4-CH.sub.3C.sub.6 H.sub.4CHCH CHCH164 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CHCH CHCH165 2-OCH.sub.3C.sub.6 H.sub.4CHCH CHCH166 4-OCH.sub.3C.sub.6 H.sub.4CHCH CHCH167 4-phenoxy-C.sub.6 H.sub.4CHCH CHCH168 C.sub.6 H.sub.5(CH.sub.2).sub.3 CHCH169 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2 CHCH170 C.sub.6 H.sub.5(CH.sub.2).sub.4 CHCH171 C.sub.6 H.sub.5(CH.sub.2).sub.5 CHCH172 C.sub.6 H.sub.5(CH.sub.2).sub.6 CHCH173 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2 CHCH174 H CH.sub.2 CH.sub. 2175 CH.sub.3 CH.sub.2 CH.sub.2176 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2177 n-C.sub.3 H.sub.7 CH.sub.2 CH.sub.2178 iso-C.sub.3 H.sub.7 CH.sub.2 CH.sub.2179 n-C.sub.4 H.sub.9 CH.sub.2 CH.sub.2180 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2181 CH.sub.3 CH.sub.2 CH(CH.sub.3) CH.sub.2 CH.sub.2182 tert.C.sub.4 H.sub.9 CH.sub.2 CH.sub.2183 CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 CH.sub.2184 (CH.sub.3).sub.3 CCH.sub.2 CH.sub.2 CH.sub.2185 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2186 CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5) CH.sub.2 CH.sub.2187 n-C.sub.5 H.sub.11 CH.sub.2 CH.sub.2188 n-C.sub.6 H.sub.13 CH.sub.2 CH.sub.2189 n-C.sub.7 H.sub.15 CH.sub.2 CH.sub.2190 n-C.sub.8 H.sub.17 CH.sub.2 CH.sub.2191 n-C.sub. 9 H.sub.19 CH.sub.2 CH.sub.2192 n-C.sub.10 H.sub.21 CH.sub.2 CH.sub.2193 n-C.sub.15 H.sub.31 CH.sub.2 CH.sub.2194 n-C.sub.17 H.sub.35 CH.sub.2 CH.sub.2195 CH.sub.2CH CH.sub.2 CH.sub.2196 CH.sub.2C(CH.sub.3) CH.sub.2 CH.sub.2197 CH.sub.3 CHCH CH.sub.2 CH.sub.2198 CH.sub.3 CHC(CH.sub.3) CH.sub.2 CH.sub.2199 (CH.sub.3).sub.2 CCH CH.sub.2 CH.sub.2200 CH.sub.2CHCH.sub.2 CH.sub.2 CH.sub.2201 CH.sub.3 CHCHCH.sub.2 CH.sub.2 CH.sub.2202 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH.sub.2203 CH.sub.3 CHCHCHCH CH.sub.2 CH.sub.2204 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH CH.sub.2 CH.sub.2205 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2206 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub. 2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2207 HCC CH.sub.2 CH.sub.2208 C.sub.6 H.sub.5CC CH.sub.2 CH.sub.2209 CH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2210 C.sub.2 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2211 CH.sub.3 CH(OCH.sub.3) CH.sub.2 CH.sub.2212 CNCH.sub.2 CH.sub.2 CH.sub.2213 cyclopropyl CH.sub.2 CH.sub.2214 cyclobutyl CH.sub.2 CH.sub.2215 cyclopentyl CH.sub.2 CH.sub.2216 cyclohexyl CH.sub.2 CH.sub.2217 1-methylcyclopropyl CH.sub.2 CH.sub.2218 2,2-dichloro-1-methyl-cyclopropyl CH.sub.2 CH.sub.2219 2,2-dichloro-3,3-dimethyl-cyclopropyl CH.sub.2 CH.sub.2220 2,2,3,3-tetramethylcyclopropyl CH.sub.2 CH.sub.2221 2-(2'-methyl-1'-propenyl-)-3,3dimethylcyclopropyl CH.sub.2 CH.sub.2222 2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl CH.sub.2 CH.sub.2223 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl CH.sub.2 CH.sub.2224 2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl CH.sub.2 CH.sub.2225 2-phenylcyclopropyl CH.sub.2 CH.sub.2226 2-(4'-chlorophenyl)cyclopropyl CH.sub.2 CH.sub.2227 2,2-dichloro-3-phenylcyclopropyl CH.sub.2 CH.sub.2228 2-carbomethoxy-cyclopropyl CH.sub.2 CH.sub.2229 ClCH.sub.2 CH.sub.2 CH.sub.2230 Cl.sub.2 CH CH.sub.2 CH.sub.2231 Cl.sub.3 C CH.sub.2 CH.sub.2232 BrCH.sub.2 CH.sub.2 CH.sub.2233 CF.sub.3 CH.sub.2 CH.sub.2234 CH.sub.3 CH(Cl) CH.sub.2 CH.sub.2235 C.sub.6 H.sub.5 (phenyl) CH.sub.2 CH.sub.2236 2-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2237 3-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2238 4-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2239 2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2240 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2241 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2242 3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub. 2 CH.sub.2243 3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2244 2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2 CH.sub.2 CH.sub.2245 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 CH.sub.2 CH.sub.2246 2-C.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.2 CH.sub.2247 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.2 CH.sub.2248 2-ClC.sub.6 H.sub.4 CH.sub.2 CH.sub.2249 3-ClC.sub.6 H.sub.4 CH.sub.2 CH.sub.2250 4-ClC.sub.6 H.sub.4 CH.sub.2 CH.sub.2251 2,4-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2252 2,5-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2253 2,6-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2254 3,4-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2255 3,5-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2256 2,4,5-Cl.sub.3C.sub.6 H.sub.2 CH.sub.2 CH.sub.2257 2,3,4,5,6-Cl.sub.5C.sub.6 CH.sub. 2 CH.sub.2258 6-F,2ClC.sub.6 H.sub.3 CH.sub.2 CH.sub.2260 2-FC.sub.6 H.sub.4 CH.sub.2 CH.sub.2261 3-FC.sub.6 H.sub.4 CH.sub.2 CH.sub.2262 4-FC.sub.6 H.sub.4 CH.sub.2 CH.sub.2263 2,4-F.sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2264 2,6-F.sub.2C.sub.6 H.sub.3 CH.sub.2 CH.sub.2265 2,3,4,5,6-F.sub.5C.sub.6 CH.sub.2 CH.sub.2266 2-BrC.sub.6 H.sub.4 CH.sub.2 CH.sub.2267 3-BrC.sub.6 H.sub.4 CH.sub.2 CH.sub.2268 4-BrC.sub.6 H.sub.4 CH.sub.2 CH.sub.2269 2-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2270 3-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2271 4-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2272 2-OCH.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2273 3-OCH.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2277 4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub. 4 CH.sub.2 CH.sub.2278 2-phenoxy-C.sub.6 H.sub.4 CH.sub.2 CH.sub.2279 3-phenoxy-C.sub.6 H.sub.4 CH.sub.2 CH.sub.2280 4-phenoxy-C.sub.6 H.sub.4 CH.sub.2 CH.sub.2281 C.sub.6 H.sub.5CH.sub.2 CH.sub.2 CH.sub.2282 2-FC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2283 3-FC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2284 4-FC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2285 2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2286 3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2287 4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2288 2-Cl,6FC.sub.6 H.sub.3CH.sub.2 CH.sub.2 CH.sub.2289 2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 CH.sub.2290 2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 CH.sub.2291 3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 CH.sub.2292 2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2 CH.sub.2 CH.sub.2293 2-CH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2294 3-CH.sub.3C.sub.6 H.sub.4CH.sub. 2 CH.sub.2 CH.sub.2295 4-CH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2296 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2297 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 CH.sub.2298 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 CH.sub.2299 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2 CH.sub.2 CH.sub.2300 2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2301 3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2302 4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2302 2-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2303 3-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2304 4-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2305 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2306 4-OC.sub. 6 H.sub.5C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2307 4-C.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2308 2-BrC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2309 3-BrC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2310 4-BrC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2311 C.sub.6 H.sub.5CH(CH.sub.3) CH.sub.2 CH.sub.2312 C.sub.6 H.sub.5CH(C.sub.2 H.sub.5) CH.sub.2 CH.sub.2313 C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.7) CH.sub.2 CH.sub.2314 C.sub.6 H.sub.5CH(OH) CH.sub.2 CH.sub.2315 2-OCH.sub.3C.sub.6 H.sub.4CH(OH) CH.sub.2 CH.sub.2316 4-OCH.sub.3C.sub.6 H.sub.4CH(OH) CH.sub.2 CH.sub.2317 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OH) CH.sub.2 CH.sub.2318 2-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3) CH.sub.2 CH.sub.2319 4-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub. 3) CH.sub.2 CH.sub.2320 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OCH.sub.3) CH.sub.2 CH.sub.2321 C.sub.6 H.sub.5CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2322 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3) CH.sub.2 CH.sub.2323 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2324 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3) CH.sub.2 CH.sub.2325 2-Cl-C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2326 3-Cl-C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2327 4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2328 C.sub.6 H.sub.5CHCH CH.sub.2 CH.sub.2329 2-ClC.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2330 3-ClC.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2331 4-ClC.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2332 2,4-Cl.sub.2 C.sub.6 H.sub.3CHCH CH.sub.2 CH.sub.2333 2-FC.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2334 4-FC.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2335 2-CH.sub.3C.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2336 4-CH.sub.3C.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2337 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2338 2-OCH.sub.3C.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2339 4-OCH.sub.3C.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2340 4-phenoxy-C.sub.6 H.sub.4CHCH CH.sub.2 CH.sub.2341 C.sub.6 H.sub.5(CH.sub.2).sub.3 CH.sub.2 CH.sub.2342 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2343 C.sub.6 H.sub.5(CH.sub.2).sub.4 CH.sub.2 CH.sub.2344 C.sub.6 H.sub.5(CH.sub.2).sub.5 CH.sub.2 CH.sub.2345 C.sub.6 H.sub.5(CH.sub.2).sub. 6 CH.sub.2 CH.sub.2346 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2347 C.sub.6 H.sub.5 O CH.sub.2 CH.sub.2348 2-ClC.sub.6 H.sub.4 O CH.sub.2 CH.sub.2349 3-ClC.sub.6 H.sub.4 O CH.sub.2 CH.sub.2350 4-ClC.sub.6 H.sub.4 O CH.sub.2 CH.sub.2351 2-CH.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2352 4-CH.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2353 2-OCH.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2354 4-OCH.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2355 2-CF.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2356 4-CF.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2357 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2358 2-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2359 4-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub. 2 CH.sub.2360 2-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2361 4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2362 2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2363 4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2364 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2365 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2366 2-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2367 4-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2368 4-FC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2369 2-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2370 4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2371 2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2372 4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2373 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2374 C.sub.6 H.sub.5 O(CH.sub.2).sub.3 CH.sub.2 CH.sub.2375 2-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.3 CH.sub.2 CH.sub.2376 4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.3 CH.sub.2 CH.sub.2377 C.sub.6 H.sub.5 O(CH.sub.2).sub.4 CH.sub.2 CH.sub.2378 2-ClC.sub.6 H.sub.4O(CH.sub.2).sub.4 CH.sub.2 CH.sub.2379 4-ClC.sub.6 H.sub.4O(CH.sub.2).sub.4 CH.sub.2 CH.sub.2380 C.sub.6 H.sub.5 O(CH.sub.2).sub.5 CH.sub.2 CH.sub.2381 2-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.5 CH.sub.2 CH.sub.2382 4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.5 CH.sub.2 CH.sub.2383 C.sub.6 H.sub.5 O(CH.sub.2).sub.6 CH.sub.2 CH.sub.2384 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 O CH.sub.2 CH.sub.2385 H CH.sub.2 O386 CH.sub.3 CH.sub.2 O387 C.sub.2 H.sub.5 CH.sub.2 O388 n-C.sub.3 H.sub.7 CH.sub.2 O389 iso-C.sub.3 H.sub.7 CH.sub.2 O390 n-C.sub.4 H.sub.9 CH.sub.2 O391 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 O392 CH.sub.3 CH.sub.2 CH(CH.sub.3) CH.sub.2 O393 tert.C.sub.4 H.sub.9 CH.sub.2 O394 CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 O395 (CH.sub.3).sub.3 CCH.sub.2 CH.sub.2 O396 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 O397 CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5) CH.sub.2 O398 n-C.sub.5 H.sub.11 CH.sub.2 O399 n-C.sub.6 H.sub.13 CH.sub.2 O400 n-C.sub.7 H.sub.15 CH.sub.2 O401 n-C.sub.8 H.sub.17 CH.sub.2 O402 n-C.sub.9 H.sub.19 CH.sub.2 O403 n-C.sub.10 H.sub.21 CH.sub.2 O404 n-C.sub.15 H.sub.31 CH.sub.2 O405 n-C.sub.17 H.sub.35 CH.sub.2 O406 CH.sub.2CH CH.sub.2 O407 CH.sub.2C(CH.sub.3) CH.sub.2 O408 CH.sub.3 CHCH CH.sub.2 O409 CH.sub.3 CHC(CH.sub.3) CH.sub.2 O410 (CH.sub.3).sub.2 CCH CH.sub.2 O411 CH.sub.2CHCH.sub.2 CH.sub.2 O412 CH.sub.3 CHCHCH.sub.2 CH.sub.2 O413 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 O414 CH.sub.3 CHCHCHCH CH.sub.2 O415 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH CH.sub.2 O416 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 O417 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 O418 HC C CH.sub.2 O419 C.sub.6 H.sub.5CC CH.sub.2 O420 CH.sub.3 OCH.sub.2 CH.sub.2 O421 C.sub.2 H.sub.5 OCH.sub.2 CH.sub.2 O422 CH.sub.3 CH(OCH.sub.3) CH.sub.2 O423 CNCH.sub.2 CH.sub.2 O424 cyclopropyl CH.sub.2 O425 cyclobutyl CH.sub.2 O426 cyclopentyl CH.sub.2 O427 cyclohexyl CH.sub.2 O428 1-methylcyclopropyl CH.sub.2 O429 2,2-dichloro-1-methyl-cyclopropyl CH.sub.2 O430 2,2-dichloro-3,3-dimethyl-cyclopropyl CH.sub.2 O431 2,2,3,3-tetramethylcyclopropyl CH.sub.2 O432 2-(2'-methyl-1'-propenyl-)-3,3-dimethylcyclopropyl CH.sub.2 O433 2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl CH.sub.2 O434 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl CH.sub.2 O435 2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl CH.sub.2 O436 2-phenylcyclopropyl CH.sub.2 O437 2-(4'-chlorophenyl)cyclopropyl CH.sub.2 O438 2,2-dichloro-3-phenylcyclopropyl CH.sub.2 O439 2-carbomethoxy-cyclopropyl CH.sub.2 O440 Cl.sub.2 CH CH.sub.2 O441 Cl.sub.2 CH CH.sub.2 O442 Cl.sub.3 C CH.sub.2 O443 BrCH.sub.2 CH.sub.2 O444 CF.sub.3 CH.sub.2 O445 CH.sub.3 CH(Cl) CH.sub.2 O446 C.sub.6 H.sub.5 (phenyl) CH.sub.2 O oil; IR (film): 1727,1602,1495,1451,1276, 1242,1208,753,735,696 cm.sup.-1447 2-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 O448 3-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 O oil; IR (film): 1738,1602,1495,1242,1160 1018,753 cm.sup.-1449 4-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 O450 2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 O451 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 O452 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 O453 3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 O454 3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 O455 2,4,6-(CH.sub.3).sub. 2C.sub.6 H.sub.2 CH.sub.2 O456 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 CH.sub.2 O457 2-C.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.2 O458 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.2 O459 2-ClC.sub.6 H.sub.4 CH.sub.2 O460 3-ClC.sub.6 H.sub.4 CH.sub.2 O oil; IR (film): 1726,1491 1451,1210,753 cm.sup.-1461 4-ClC.sub.6 H.sub.4 CH.sub.2 O462 2,4-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 O463 2,5-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 O464 2,6-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 O465 3,4-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 O466 3,5-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2 O467 2,4,5-Cl.sub.3C.sub.6 H.sub.2 CH.sub.2 O468 2,3,4,5,6-Cl.sub.5C.sub.6 CH.sub.2 O469 6-F,2-ClC.sub.6 H.sub.3 CH.sub.2 O470 2-FC.sub.6 H.sub.4 CH.sub.2 O471 3-FC.sub.6 H.sub.4 CH.sub.2 O472 2,4-F.sub.2C.sub.6 H.sub.3 CH.sub.2 O473 2,6-F.sub.2C.sub.6 H.sub.3 CH.sub.2 O474 2,6-F.sub.2C.sub.6 H.sub.3 CH.sub.2 O475 2,3,4,5,6-E.sub.5C.sub.6 CH.sub.2 O476 2-BrC.sub.6 H.sub.4 CH.sub.2 O477 3-BrC.sub.6 H.sub.4 CH.sub.2 O478 4-BrC.sub.6 H.sub.4 CH.sub.2 O479 2-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 O480 3-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 O481 4-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 O482 2-OCH.sub.3C.sub.6 H.sub.4 CH.sub.2 O483 3-OCH.sub.3C.sub.6 H.sub.4 CH.sub.2 O484 4-OCH.sub.3C.sub.6 H.sub.4 CH.sub.2 O485 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2 O486 3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2 CH.sub.2 O487 4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4 CH.sub.2 O488 2-phenoxy-C.sub.6 H.sub.4 CH.sub.2 O489 3-phenoxy-C.sub.6 H.sub.4 CH.sub.2 O490 4-phenoxy-C.sub.6 H.sub.4 CH.sub.2 O491 C.sub.6 H.sub.5CH.sub.2 CH.sub.2 O492 2-FC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O493 3-FC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O494 4-FC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O495 2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O496 3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O497 4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O498 2-Cl,6FC.sub.6 H.sub.3CH.sub.2 CH.sub.2 O499 2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 O500 2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 O501 3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 O502 2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2 CH.sub.2 O503 2-CH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O504 3-CH.sub. 3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O505 4-CH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O506 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O507 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 O508 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 CH.sub.2 O509 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2 CH.sub.2 O510 2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O511 3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O512 4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O513 2-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O514 3-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O515 4-CF.sub.3C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O516 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O517 4-OC.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.2 CH.sub.2 O518 4-C.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2 CH.sub.2 O519 2-BrC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O520 3-BrC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O521 4-BrC.sub.6 H.sub.4CH.sub.2 CH.sub.2 O522 C.sub.6 H.sub.5CH(CH.sub.3) CH.sub.2 O523 C.sub.6 H.sub.5CH(C.sub.2 H.sub.5) CH.sub.2 O524 C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.7) CH.sub.2 O525 C.sub.6 H.sub.5CH(OH) CH.sub.2 O526 2-OCH.sub.3C.sub.6 H.sub.4CH(OH) CH.sub.2 O527 4-OCH.sub.3C.sub.6 H.sub.4CH(OH) CH.sub.2 O528 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OH) CH.sub.2 O529 2-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3) CH.sub.2 O530 4-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3) CH.sub.2 O531 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OCH.sub.3) CH.sub.2 O532 C.sub.6 H.sub.5CH.sub.2 CH.sub.2 CH.sub.2 O533 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3) CH.sub.2 O534 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2 O535 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3) CH.sub.2 O536 2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2 O537 3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2 O538 4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 CH.sub.2 O539 C.sub.6 H.sub.5CHCH CH.sub.2 O540 2-ClC.sub.6 H.sub.4CHCH CH.sub.2 O541 3-ClC.sub.6 H.sub.4CHCH CH.sub.2 O542 4-ClC.sub.6 H.sub.4CHCH CH.sub.2 O543 2,4-Cl.sub.2C.sub.6 H.sub.3CHCH CH.sub.2 O545 2-FC.sub.6 H.sub.4CHCH CH.sub.2 O546 4-FC.sub.6 H.sub.4CH CH CH.sub.2 O547 2-CH.sub.3C.sub.6 H.sub.4CHCH CH.sub.2 O548 4-CH.sub.3C.sub.6 H.sub.4CHCH CH.sub.2 O549 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CHCH CH.sub.2 O550 2-OCH.sub.3C.sub.6 H.sub.4CHCH CH.sub.2 O551 4-OCH.sub.3C.sub.6 H.sub.4CHCH CH.sub.2 O552 4-phenoxy-C.sub.6 H.sub.4CHCH CH.sub.2 O553 C.sub.6 H.sub.5(CH.sub.2).sub.3 CH.sub.2 O554 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 O555 C.sub.6 H.sub.5(CH.sub.2).sub.4 CH.sub.2 O556 C.sub.6 H.sub.5(CH.sub.2).sub.5 CH.sub.2 O557 C.sub.6 H.sub.5(CH.sub.2).sub.6 CH.sub.2 O558 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 O559 H OCH.sub.2560 CH.sub.3 OCH.sub.2561 C.sub.2 H.sub.5 OCH.sub.2562 n-C.sub.3 H.sub.7 OCH.sub.2563 iso-C.sub.3 H.sub.7 OCH.sub.2564 n-C.sub.4 H.sub.9 OCH.sub.2565 (CH.sub.3).sub.2 CHCH.sub.2 OCH.sub.2566 CH.sub.3 CH.sub.2 CH(CH.sub.3) OCH.sub.2567 tert.C.sub.4 H.sub.9 OCH.sub.2568 CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 OCH.sub.2569 (CH.sub.3).sub.3 CCH.sub.2 OCH.sub.2570 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 OCH.sub.2571 CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5) OCH.sub.2572 n-C.sub.5 H.sub.11 OCH.sub.2573 n-C.sub.6 H.sub.13 OCH.sub.2574 n-C.sub.7 H.sub.15 OCH.sub.2575 n-C.sub.8 H.sub.17 OCH.sub.2__________________________________________________________________________
__________________________________________________________________________576 n-C.sub.9 H.sub.19 OCH.sub.2577 n-C.sub.10 H.sub.21 OCH.sub.2578 n-C.sub.15 H.sub.31 OCH.sub.2579 n-C.sub.17 H.sub.35 OCH.sub.2580 CH.sub.2CH OCH.sub.2581 CH.sub.2C(CH.sub.3) OCH.sub.2582 CH.sub.3 CHCH OCH.sub.2583 CH.sub.3 CHC(CH.sub.3) OCH.sub.2584 (CH.sub.3).sub.2 CCH OCH.sub.2585 CH.sub.2CHCH.sub.2 OCH.sub.2586 CH.sub.3 CHCHCH.sub.2 OCH.sub.2587 (CH.sub.3).sub.2 CCHCH.sub.2 OCH.sub.2588 CH.sub.3 CHCHCHCH OCH.sub.2589 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH OCH.sub.2590 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 OCH.sub.2591 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 OCH.sub.2592 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub. 2 CH(CH.sub.3)CH.sub.2 OCH.sub.2593 CH.sub.3 OCH.sub.2 OCH.sub.2594 C.sub.2 H.sub.5 OCH.sub.2 OCH.sub.2595 CH.sub.3 CH(OCH.sub.3) OCH.sub.2596 CNCH.sub.2 OCH.sub.2597 cyclopropyl OCH.sub.2598 cyclobutyl OCH.sub.2599 cyclopentyl OCH.sub.2600 cyclohexyl OCH.sub.2601 1-methylcyclopropyl OCH.sub.2602 2,2-dichloro-1-methyl-cyclopropyl OCH.sub.2603 2,2-dichloro-3,3-dimethyl-cyclopropyl OCH.sub.2604 2,2,3,3-tetramethylcyclopropyl OCH.sub.2605 2-(2'-methyl-1'-propenyl-)-3,3-dimethylcyclopropyl OCH.sub.2606 2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl OCH.sub.2607 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl OCH.sub.2608 2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl OCH.sub.2609 2-phenylcyclopropyl OCH.sub.2610 2-(4'-chlorophenyl)cyclopropyl OCH.sub.2611 2,2-dichloro-3-phenylcyclopropyl OCH.sub.2612 2-carbomethoxy-cyclopropyl OCH.sub.2613 Cl.sub.2 CH OCH.sub.2614 Cl.sub.2 CH OCH.sub.2615 Cl.sub.3 C OCH.sub.2616 BrCH.sub.2 OCH.sub.2617 CF.sub.3 OCH.sub.2618 CH.sub.3 CH(Cl) OCH.sub.2619 C.sub. 6 H.sub.5 (phenyl) OCH.sub.2620 2-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2621 3-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2622 4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2623 2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3 OCH.sub.2624 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 OCH.sub.2625 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3 OCH.sub.2626 3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 OCH.sub.2627 3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3 OCH.sub.2628 2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2 OCH.sub.2629 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 OCH.sub.2630 2-C.sub.6 H.sub.5C.sub.6 H.sub.4 OCH.sub.2631 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 OCH.sub.2632 2-ClC.sub.6 H.sub.4 OCH.sub.2 oil; .sup.1 H-NMR (CDCl.sub.3): .delta. = 3.75(3H),5.03(2H), 2 5.83(2H),6.58(1H),6.90(1H), 1 7.0-7.6(8H)633 3-Cl C.sub.6 H.sub.4 OCH.sub.2634 4-ClC.sub.6 H.sub.4 OCH.sub.2635 2,4-Cl.sub.2C.sub.6 H.sub.3 OCH.sub.2636 2,5-Cl.sub.2C.sub.6 H.sub.3 OCH.sub.2637 2,6-Cl.sub.2C.sub.6 H.sub.3 OCH.sub.2638 3,4-Cl.sub.2C.sub.6 H.sub.3 OCH.sub.2639 3,5-Cl.sub.2C.sub.6 H.sub.3 OCH.sub.2640 2,4,5-Cl.sub.3C.sub.6 H.sub.2 OCH.sub.2641 2,3,4,5,6-Cl.sub.5C.sub.6 OCH.sub.2642 6-F,2-ClC.sub.6 H.sub.3 OCH.sub.2643 2-FC.sub.6 H.sub.4 OCH.sub.2644 3-FC.sub.6 H.sub.4 OCH.sub.2645 4-FC.sub.6 H.sub.4 OCH.sub.2646 2,4-F.sub.2C.sub.6 H.sub.3 OCH.sub.2647 2,6-F.sub.2C.sub.6 H.sub.3 OCH.sub.2648 2,3,4,5,6-F.sub.5C.sub.6 OCH.sub.2649 2-BrC.sub.6 H.sub.4 OCH.sub.2 oil; .sup.1 H-NMR (CDCl.sub.3): .delta. = 3.77(3H),5.03(2H), . 5.83(2H),6.60(1H),6.83(2H), 7.1-7.7(6H)650 3-BrC.sub.6 H.sub.4 OCH.sub.2651 4-BrC.sub.6 H.sub.4 OCH.sub.2652 2-CF.sub.3C.sub.6 H.sub.4 OCH.sub.2653 3-CF.sub.3C.sub.6 H.sub.4 OCH.sub.2654 4-CF.sub.3C.sub.6 H.sub.4 OCH.sub.2655 2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2656 3-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2657 4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2658 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3 OCH.sub.2659 3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2 OCH.sub.2660 4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4 OCH.sub.2661 2-phenoxy-C.sub.6 H.sub.4 OCH.sub.2662 3-phenoxy-C.sub.6 H.sub.4 OCH.sub.2663 4-phenoxy-C.sub.6 H.sub.4 OCH.sub.2664 C.sub.6 H.sub.5CH.sub.2 OCH.sub.2665 2-FC.sub.6 H.sub.4CH.sub.2 OCH.sub.2666 3-FC.sub.6 H.sub.4CH.sub.2 OCH.sub.2667 4-FC.sub.6 H.sub.4CH.sub.2 OCH.sub. 2668 2-ClC.sub.6 H.sub.4CH.sub.2 OCH.sub.2669 3-ClC.sub.6 H.sub.4CH.sub.2 OCH.sub.2670 4-ClC.sub.6 H.sub.4CH.sub.2 OCH.sub.2671 2-Cl,6FC.sub.6 H.sub.3CH.sub.2 OCH.sub.2672 2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 OCH.sub.2673 2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 OCH.sub.2674 3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 OCH.sub.2675 2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2 OCH.sub.2676 2-CH.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2677 3-CH.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2678 4-CH.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2679 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 OCH.sub.2680 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 OCH.sub.2681 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 OCH.sub.2682 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2 OCH.sub.2683 2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2684 3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2685 4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2686 2-CF.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2687 3-CF.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2688 4-CF.sub.3C.sub.6 H.sub.4CH.sub.2 OCH.sub.2689 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 OCH.sub.2690 4-OC.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2 OCH.sub.2691 4-C.sub.6 H.sub.5CH.sub.2 OCH.sub.2692 2-BrC.sub.6 H.sub.4CH.sub.2 OCH.sub.2693 3-BrC.sub.6 H.sub.4CH.sub.2 OCH.sub.2694 4-BrC.sub.6 H.sub.4CH.sub.2 OCH.sub.2695 C.sub.6 H.sub.5CH(CH.sub.3) OCH.sub.2696 C.sub.6 H.sub.5CH(C.sub.2 H.sub.5) OCH.sub.2697 C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.) OCH.sub.2698 C.sub.6 H.sub.5CH.sub.2 CH.sub.2 OCH.sub.2699 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3) OCH.sub.3700 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 OCH.sub.2701 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3) OCH.sub.2702 2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 OCH.sub.2703 3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 OCH.sub.2704 4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.3 OCH.sub.2705 C.sub.6 H.sub.5CHCH OCH.sub.2706 C.sub.6 H.sub.5(CH.sub.2).sub.3 OCH.sub.2707 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2 OCH.sub.2708 C.sub.6 H.sub.5(CH.sub.2).sub.4 OCH.sub.2709 C.sub.6 H.sub.5(CH.sub.2).sub.5 OCH.sub.2710 C.sub.6 H.sub.5(CH.sub.2).sub.6 OCH.sub.2711 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2 OCH.sub.2712 H COOCH.sub.2713 CH.sub.3 COOCH.sub.2714 C.sub.2 H.sub.5 COOCH.sub.2715 n-C.sub.3 H.sub.7 COOCH.sub.2716 iso-C.sub.3 H.sub.7 COOCH.sub.2717 n-C.sub.4 H.sub.9 COOCH.sub.2718 (CH.sub.3).sub.2 CHCH.sub.2 COOCH.sub.2719 CH.sub.3 CH.sub.2 CH(CH.sub.3) COOCH.sub.2720 tert.C.sub.4 H.sub.9 COOCH.sub.2 oil; IR (film): 1727,1480, 1281,1150,771 cm.sup.-1721 CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 COOCH.sub.2722 (CH.sub.3).sub.3 CCH.sub.2 COOCH.sub.2723 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 COOCH.sub.2724 CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5) COOCH.sub.2725 n-C.sub.5 H.sub.11 COOCH.sub.2726 n-C.sub.6 H.sub.13 COOCH.sub.2727 n-C.sub.7 H.sub.15 COOCH.sub.2728 n-C.sub.8 H.sub.17 COOCH.sub.2729 n-C.sub.9 H.sub.19 COOCH.sub.2730 n-C.sub.10 H.sub.21 COOCH.sub.2731 n-C.sub.15 H.sub.31 COOCH.sub.2732 n-C.sub.17 H.sub.35 COOCH.sub.2733 CH.sub.2CH COOCH.sub.2734 CH.sub.2C(CH.sub.3) COOCH.sub.2735 CH.sub.3 CHCH COOCH.sub.2736 CH.sub.3 CHC(CH.sub.3) COOCH.sub.2737 (CH.sub.3).sub.2 CCH COOCH.sub.2738 CH.sub.2CHCH.sub.2 COOCH.sub.2739 CH.sub.3 CHCHCH.sub.2 COOCH.sub.2740 (CH.sub.3).sub.2 CCHCH.sub.2 COOCH.sub.2741 CH.sub.3 CHCHCHCH COOCH.sub.2742 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH COOCH.sub.2743 (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 COOCH.sub.2744 (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 COOCH.sub.2745 HC C COOCH.sub.2746 C.sub.6 H.sub.5CC COOCH.sub.2747 CH.sub.3 OCH.sub.2 COOCH.sub.2748 C.sub.2 H.sub.5 OCH.sub.2 COOCH.sub.2749 CH.sub.3 CH(OCH.sub.3) COOCH.sub.2750 CNCH.sub.2 COOCH.sub.2751 cyclopropyl COOCH.sub.2 oil; IR (Film): 2958,1726, 1399,1168,1082,772 cm.sup.-1752 cyclobutyl COOCH.sub.2753 cyclopentyl COOCH.sub.2754 cyclohexyl COOCH.sub.2755 1-methylcyclopropyl COOCH.sub.2 oil; IR (film): 1724,1323,1214,1197, 1157,771,75 cm.sup.-1756 2,2-dichloro-1-methyl-cyclopropyl COOCH.sub.2757 2,2-dichloro-3,3-dimethyl-cyclopropyl COOCH.sub.2758 2,2,3,3-tetramethylcyclopropyl COOCH.sub.2759 2-(2'-methyl-1'-propenyl-)-3,3-dimethylcyclopropyl COOCH.sub.2760 2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl COOCH.sub.2761 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl COOCH.sub.2762 2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl COOCH.sub.2763 2-phenylcyclopropyl COOCH.sub.2764 2-(4'-chlorophenyl)cyclopropyl COOCH.sub.2765 2,2-dichloro-3-phenylcyclopropyl COOCH.sub.2766 2-carbomethoxy-cyclopropyl COOCH.sub.2767 Cl.sub.2 CH COOCH.sub.2768 Cl.sub.2 CH COOCH.sub.2769 Cl.sub.3 C COOCH.sub.2770 BrCH.sub.2 COOCH.sub.2771 CF.sub.3 COOCH.sub.2772 CH.sub.3 CH(Cl) COOCH.sub.2773 C.sub.6 H.sub.5 (phenyl) COOCH.sub.2 oil; IR (film) 1722,1451,1314,1270 1213,1110,713 cm.sup.-1774 2-CH.sub.3C.sub.6 H.sub.4 COOCH.sub.2775 3-CH.sub.3C.sub.6 H.sub.4 COOCH.sub.2776 4-CH.sub.3C.sub.6 H.sub.4 COOCH.sub.2777 2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3 COOCH.sub.2778 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 COOCH.sub.2779 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3 COOCH.sub.2780 3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 COOCH.sub.2781 3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3 COOCH.sub.2782 2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2 COOCH.sub.2783 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 COOCH.sub.2784 2-C.sub.6 H.sub.5C.sub.6 H.sub.4 COOCH.sub.2785 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 COOCH.sub.2786 2-ClC.sub.6 H.sub.4 COOCH.sub.2787 3-ClC.sub.6 H.sub.4 COOCH.sub.2788 4-ClC.sub.6 H.sub.4 COOCH.sub.2789 2,4-Cl.sub.2C.sub.6 H.sub.3 COOCH.sub.2790 2,5-Cl.sub.2C.sub.6 H.sub.3 COOCH.sub.2791 2,6-Cl.sub.2C.sub.6 H.sub.3 COOCH.sub.2792 3,4-Cl.sub.2C.sub.6 H.sub.3 COOCH.sub.2793 3,5-Cl.sub.2C.sub.6 H.sub.3 COOCH.sub.2794 2,4,5-Cl.sub.3C.sub.6 H.sub.3 COOCH.sub.2795 2,3,4,5,6-Cl.sub.5C.sub.6 COOCH.sub.2796 6-F,2-ClC.sub.6 H.sub.3 COOCH.sub.2797 2-FC.sub.6 H.sub.4 COOCH.sub.2798 3-FC.sub.6 H.sub.4 COOCH.sub.2799 4-FC.sub.6 H.sub.4 COOCH.sub.2800 2,4-F.sub.2C.sub.6 H.sub.3 COOCH.sub.2801 2,6-F.sub.2C.sub.6 H.sub.3 COOCH.sub.2802 2,3,4,5,6-F.sub.5C.sub.6 COOCH.sub.2803 2-BrC.sub.6 H.sub.4 COOCH.sub.2804 3-BrC.sub.6 H.sub.4 COOCH.sub.2805 4-BrC.sub.6 H.sub.4 COOCH.sub.2806 2-CF.sub.3C.sub.6 H.sub.4 COOCH.sub.2807 3-CF.sub.3C.sub.6 H.sub.4 COOCH.sub.2808 4-CF.sub.3C.sub.6 H.sub.4 COOCH.sub.2809 2-OCH.sub.3C.sub.6 H.sub.4 COOCH.sub.2810 3-OCH.sub.3C.sub.6 H.sub.4 COOCH.sub.2811 4-OCH.sub.3C.sub.6 H.sub.4 COOCH.sub.2812 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3 COOCH.sub.2813 3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.3 COOCH.sub.2814 4-t-C.sub.4 H.sub. 9 OC.sub.6 H.sub.4 COOCH.sub.2815 2-phenoxy-C.sub.6 H.sub.4 COOCH.sub.2816 3-phenoxy-C.sub.6 H.sub.4 COOCH.sub.2817 4-phenoxy-C.sub.6 H.sub.4 COOCH.sub.2818 C.sub.6 H.sub.5CH.sub.2 COOCH.sub.2819 2-FC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2820 3-FC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2821 4-FC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2822 2-ClC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2823 3-ClC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2824 4-ClC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2825 2-Cl,6FC.sub.6 H.sub.3CH.sub.2 COOCH.sub.2826 2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 COOCH.sub.2827 2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 COOCH.sub.2828 3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 COOCH.sub.2829 2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2 COOCH.sub.2830 2-CH.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2831 3-CH.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2832 4-CH.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2833 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2834 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 COOCH.sub.2835 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2 COOCH.sub.2836 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2 COOCH.sub.2837 2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2838 3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2839 4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2840 2-CF.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2841 3-CF.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2842 4-CF.sub.3C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2843 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub. 2 COOCH.sub.2844 4-OC.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2845 4-C.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2 COOCH.sub.2846 2-BrC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2847 3-BrC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2848 4-BrC.sub.6 H.sub.4CH.sub.2 COOCH.sub.2849 C.sub.6 H.sub.5CH(CH.sub.3) COOCH.sub.2850 C.sub.6 H.sub.5CH(C.sub.2 H.sub.5) COOCH.sub.2851 C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.7) COOCH.sub.2852 C.sub.6 H.sub.5CH(OH) COOCH.sub.2853 2-OCH.sub.3C.sub.6 H.sub.4CH(OH) COOCH.sub.2854 4-OCH.sub.3C.sub.6 H.sub.4CH(OH) COOCH.sub.2855 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OH) COOCH.sub.2856 2-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3) COOCH.sub.2857 4-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3) COOCH.sub. 2858 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OCH.sub.3) COOCH.sub.2859 C.sub.6 H.sub.5CH.sub.2 CH.sub.2 COOCH.sub.2860 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3) COOCH.sub.2861 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2 COOCH.sub.2862 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3) COOCH.sub.2863 2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 COOCH.sub.2864 3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2 COOCH.sub.2865 4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.3 COOCH.sub.2866 C.sub.6 H.sub.5CHCH COOCH.sub.2 oil; IR (film) 1719,1637,1311,1204 1164,768 cm.sup.-1867 2-ClC.sub.6 H.sub.4CHCH COOCH.sub.2868 3-ClC.sub.6 H.sub.4CHCH COOCH.sub.2869 4-ClC.sub.6 H.sub.4CHCH COOCH.sub.2870 2,4-Cl.sub. 2C.sub.6 H.sub.3CHCH COOCH.sub.2871 2-FC.sub.6 H.sub.4CHCH COOCH.sub.2872 4-FC.sub.6 H.sub.4CHCH COOCH.sub.2873 2-CH.sub.3C.sub.6 H.sub.4CHCH COOCH.sub.2874 4-CH.sub.3C.sub.6 H.sub.4CHCH COOCH.sub.2875 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CHCH COOCH.sub.2876 2-OCH.sub.3C.sub.6 H.sub.4CHCH COOCH.sub.2877 4-OCH.sub.3C.sub.6 H.sub.4CHCH COOCH.sub.2878 4-Phenoxy-C.sub.6 H.sub.4CHCH COOCH.sub.2879 C.sub.6 H.sub.5(CH.sub.2).sub.3 COOCH.sub.2880 C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2 COOCH.sub.2881 C.sub.6 H.sub.5(CH.sub.2).sub.4 COOCH.sub.2882 C.sub.6 H.sub.5(CH.sub.2).sub.5 COOCH.sub.2883 C.sub.6 H.sub.5(CH.sub.2).sub.6 COOCH.sub.2884 4-t-C.sub.4 H.sub.9C.sub. 6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2 COOCH.sub.2885 C.sub.6 H.sub.5 CC886 2-ClC.sub.6 H.sub.4 CC887 3-ClC.sub.6 H.sub.4 CC888 4-ClC.sub.6 H.sub.4 CC889 C.sub.6 H.sub.5 OCH.sub.2 CC890 2-ClC.sub.6 H.sub.5 OCH.sub.2 CC891 3-ClC.sub.6 H.sub.5 OCH.sub.2 CC892 4-ClC.sub.6 H.sub.5 OCH.sub.2 CC893 CH.sub.3 OOC CC894 t-C.sub.4 H.sub.9 OOC C C895 C.sub.6 H.sub.6 CH.sub.2896 2-FC.sub.6 H.sub.4 CH.sub.2897 3-FC.sub.6 H.sub.4 CH.sub.2898 4-FC.sub.6 H.sub.4 CH.sub.2899 2-ClC.sub.6 H.sub.4 CH.sub.2900 3-ClC.sub.6 H.sub.4 CH.sub.2901 4-ClC.sub.6 H.sub.4 CH.sub.2902 2Cl,6FC.sub.6 H.sub.3 CH.sub.2903 2,4-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2904 2,6-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2905 3,5-Cl.sub.2C.sub.6 H.sub.3 CH.sub.2906 2,4,6-Cl.sub.3C.sub.6 H.sub.2 CH.sub.2907 2-CH.sub.3C.sub.6 H.sub.4 CH.sub.2908 3-CH.sub.3C.sub.6 H.sub.4 CH.sub.2909 4-CH.sub.3C.sub.6 H.sub.4 CH.sub.2910 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 CH.sub.2911 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2912 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3 CH.sub.2913 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2 CH.sub.2914 2-OCH.sub.3C.sub.6 H.sub.4 CH.sub.2915 3-OCH.sub.3C.sub.6 H.sub.4 CH.sub.2916 4-OCH.sub.3C.sub.6 H.sub.4 CH.sub.2917 2-CF.sub.3C.sub.6 H.sub.4 CH.sub.2918 3-CF.sub.3C.sub.6 H.sub.4 CH.sub.2919 4-CF.sub.3C.sub.6 H.sub.4 CH.sub.2920 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 CH.sub.2921 4-OC.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.2922 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.2923 2-BrC.sub.6 H.sub.4 CH.sub.2924 4-BrC.sub.6 H.sub.4 CH.sub.2 925 Br CH.sub.2 v. specification for data926 Br.sup.- (C.sub.6 H.sub.5).sub.3 P.sup.+ CH.sub.2927 Cl.sup.- (C.sub.6 H.sub.5).sub.3 P.sup.+ CH.sub.2928 Br.sub.2 ##STR6##929 Cl.sub.2 ##STR7##930 OCH --931 iso-C.sub.3 H.sub.7 O932 CH.sub.3 CH.sub.2 CH(CH.sub.3) O933 ter.C.sub.4 H.sub.9 O934 CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 O935 CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5) O936 CH.sub.2CHCH.sub.2 O937 CH.sub.3 CHCHCH.sub.2 O938 (CH.sub.3).sub.2 CCHCH.sub.2 O939 CH.sub.3 OCH.sub.2 O940 CNCH.sub.2 O941 cyclopropyl O942 cyclobutyl O943 cyclopentyl O944 cyclohexyl O945 1-methylcyclohexyl O946 1-methylcyclopropyl O947 Cl.sub.3 C O948 CF.sub.3 C O949 C.sub.6 H.sub.5 (phenyl) O950 2-CH.sub.3C.sub.6 H.sub.4 O951 3-CH.sub.3C.sub.6 H.sub.4 O952 4-CH.sub.3C.sub.6 H.sub.4 O953 2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3 O954 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 O955 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3 O956 3,4-(CH.sub. 3).sub.2C.sub.6 H.sub.3 O957 3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3 O958 2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2 O959 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 O960 2-C.sub.6 H.sub.5C.sub.6 H.sub.4 O961 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 O962 2-ClC.sub.6 H.sub.4 O963 3-ClC.sub.6 H.sub.4 O964 4-ClC.sub.6 H.sub.4 O965 2,4-Cl.sub.2C.sub.6 H.sub.3 O966 2,5-Cl.sub.2C.sub.6 H.sub.3 O967 2,6-Cl.sub.2C.sub.6 H.sub.3 O968 3,4-Cl.sub.2C.sub.6 H.sub.3 O969 3,5-Cl.sub.2C.sub.6 H.sub.3 O970 2,4,5-Cl.sub.3C.sub.6 H.sub.2 O971 2,3,4,5,6-Cl.sub.5C.sub.6 O972 6-F,2-ClC.sub.6 H.sub.3 O973 2-FC.sub.6 H.sub.4 O974 3-FC.sub.6 H.sub.4 O975 4-FC.sub.6 H.sub.4 O976 2,4-F.sub.2C.sub.6 H.sub.3 O977 2,6-F.sub.2C.sub.6 H.sub.3 O978 2,3,4,5,6-F.sub.5C.sub.6 O979 2-BrC.sub.6 H.sub.4 O980 3-BrC.sub.6 H.sub.4 O981 4-BrC.sub. 6 H.sub.4 O982 2-CF.sub.3C.sub.6 H.sub.4 O983 3-CF.sub.3C.sub.6 H.sub.4 O984 4-CF.sub.3C.sub.6 H.sub.4 O985 2-OCH.sub.3C.sub.6 H.sub.4 O986 3-OCH.sub.3C.sub.6 H.sub.4 O987 4-OCH.sub.3C.sub.6 H.sub.4 O988 3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3 O989 3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2 O990 4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4 O991 2-phenoxy-C.sub.6 H.sub.4 O992 3-phenoxy-C.sub.6 H.sub.4 O993 4-phenoxy-C.sub.6 H.sub.4 O994 C.sub.6 H.sub.5 SCH.sub.2995 2-FC.sub.6 H.sub.4 SCH.sub.2996 3-FC.sub.6 H.sub.4 SCH.sub.2997 4-FC.sub.6 H.sub.4 SCH.sub.2998 2-ClC.sub.6 H.sub.4 SCH.sub.2999 3-ClC.sub.6 H.sub.4 SCH.sub.21000 4-ClC.sub.6 H.sub.4 SCH.sub.21001 2Cl,6FC.sub.6 H.sub.3 SCH.sub.21002 2,4-Cl.sub.2C.sub.6 H.sub.3 SCH.sub.21003 2,6-Cl.sub.2C.sub.6 H.sub.3 SCH.sub. 21004 3,5-Cl.sub.2C.sub.6 H.sub.3 SCH.sub.21005 2,4,6-Cl.sub.3C.sub.6 H.sub.2 SCH.sub.21006 2-CH.sub.3C.sub.6 H.sub.4 SCH.sub.21007 3-CH.sub.3C.sub.6 H.sub.4 SCH.sub.21008 4-CH.sub.3C.sub.6 H.sub.4 SCH.sub.21009 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 SCH.sub.21010 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3 SCH.sub.21011 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3 SCH.sub.21012 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2 SCH.sub.21013 2-OCH.sub.3C.sub.6 H.sub.4 SCH.sub.21014 3-OCH.sub.3C.sub.6 H.sub.4 SCH.sub.21015 4-OCH.sub.3C.sub.6 H.sub.4 SCH.sub.21016 2-CF.sub.3C.sub.6 H.sub.4 SCH.sub.21017 3-CF.sub.3C.sub.6 H.sub.4 SCH.sub.21018 4-CF.sub.3C.sub.6 H.sub.4 SCH.sub.31019 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 SCH.sub.21020 4-O-C.sub.6 H.sub.5C.sub.6 H.sub.4 SCH.sub.21021 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 SCH.sub.21022 2-BrC.sub.6 H.sub.4 SCH.sub.21023 4-BrC.sub.6 H.sub.4 SCH.sub.21024 C.sub.6 H.sub.5 S1025 2-ClC.sub.6 H.sub.4 S1026 3-ClC.sub.6 H.sub.4 S1027 4-ClC.sub.6 H.sub.4 S1028 2-CH.sub.3C.sub.6 H.sub.4 S1029 4-CH.sub.3C.sub.6 H.sub.4 S1030 4-C.sub.6 H.sub.5C.sub.6 H.sub.5 S1031 CH.sub.3 S1032 C.sub.6 H.sub.5 O CH.sub.2 CH.sub.2 O1033 2-ClC.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1034 3-ClC.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1035 4-ClC.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1036 2-CH.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1037 4-CH.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1038 2-OCH.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1039 4-OCH.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1040 2-CF.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1041 4-CF.sub.3C.sub.6 H.sub.4 O CH.sub.2 CH.sub.2 O1042 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2 O1043 2-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 O1044 4-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 O1045 2-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 O1046 4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 O1047 2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 O1048 4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 O1049 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 O1050 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1051 2-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1052 4-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1053 4-FC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1054 2-CH.sub.2C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1055 4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1056 2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1057 4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1058 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O1059 C.sub.6 H.sub.5 O(CH.sub.2).sub.3 CH.sub.2 CH.sub.2 O1060 2-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.3 CH.sub.2 CH.sub.2 O1061 4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.3 CH.sub.2 CH.sub.2 O1062 C.sub.6 H.sub.5 O(CH.sub.2).sub.4 CH.sub.2 CH.sub.2 O1063 2-ClC.sub.6 H.sub.4O(CH.sub.2).sub.4 CH.sub.2 CH.sub.2 O1064 4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.4 CH.sub.2 CH.sub.2 O1065 C.sub.6 H.sub.5 O(CH.sub.2).sub.5 CH.sub.2 CH.sub.2 O1066 2-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.5 CH.sub.2 CH.sub.2 O1067 4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.5 CH.sub.2 CH.sub.2 O1068 C.sub.6 H.sub.5 O(CH.sub.2).sub.6 CH.sub.2 CH.sub.2 O1069 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 O CH.sub.2 CH.sub.2 O1070 C.sub.6 H.sub.5 COO1071 2-ClC.sub.6 H.sub.4 COO1072 3-ClC.sub.6 H.sub.4 COO1073 4-ClC.sub.6 H.sub.4 COO1074 2-CH.sub.3C.sub.6 H.sub.4 COO1075 4-CH.sub.3C.sub.6 H.sub.4 COO1076 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 COO1077 C.sub.6 H.sub.5 CO O1078 2-ClC.sub.6 H.sub.4 COO1079 3-ClC.sub.6 H.sub.4 COO1080 4-ClC.sub.6 H.sub.4 COO1081 2-CH.sub.3C.sub.6 H.sub.4 COO1082 CH.sub.3 COO1083 t-C.sub.4 H.sub.9 COO1084 CH.sub.2 C.sub.6 H.sub.5 COO1085 C.sub.6 H.sub.5 HNCOO1086 2-ClC.sub.6 H.sub.4 HNCOO1087 4-ClC.sub.6 H.sub.4 HNCOO1088 C.sub.6 H.sub.11 HNCOO1089 n-C.sub.4 H.sub.9 HNCOO1090 2-furyl CHCH1091 5-nitro-2-furyl CHCH1092 5-chloro-2-furyl CHCH1093 2-(2'-furyl)-ethenyl CHCH1094 2-(5'-nitro-2'-furyl)ethenyl CHCH1095 3-furyl CHCH1096 5-nitro-3-furyl CHCH1097 5-chloro-3-furyl CHCH1098 2-(3'-furyl)ethenyl CHCH1099 2-(5'-nitro-3'-furyl)ethenyl CHCH1100 benzofuran-2-yl CHCH1101 benzofuran-3-yl CHCH1102 2-thienyl CHCH1103 5-nitro-2-thienyl CHCH1104 5-chloro-2-thienyl CHCH1105 2-(2'-thienyl)ethenyl CHCH1106 2-(5'-nitro-2'-thienyl)ethenyl CHCH1107 3-thienyl CHCH1108 5-nitro-3-thienyl CHCH1109 5-chloro-3-thienyl CHCH1110 2-(3'-thienyl)ethenyl CHCH1111 2-(5'-nitro-3'-thienyl)ethenyl CHCH1112 benzothien-2-yl CHCH1113 benzothien-3-yl CHCH1114 N-methyl-pyrrol-2-yl CHCH1115 N-methyl-pyrrol-3-yl CHCH1116 N-methyl-pyrazol-3-yl CHCH1117 N-methyl-pyrazol-4-yl CHCH1118 N-methyl-pyrazol-5-yl CHCH1119 N-methyl-imidazol-2-yl CHCH1120 N-methyl-imidazol-4-yl CHCH1121 N-methyl-imidazol-5-yl CHCH1122 1-methyl-1,2,3-triazol-4-yl CHCH1123 1-methyl-1,2,3-triazol-5-yl CHCH1124 1-methyl-1,2,4-triazol-3-yl CHCH1125 1-methyl-1,2,4-triazol-5-yl CHCH1126 1-methyl-tetrazol-5-yl CHCH1127 isoxazol-3-yl CHCH1128 isoxazol-4-yl CHCH1129 isoxazol-5-yl CHCH1130 benisoxazol-3-yl CHCH1131 benzoxazol-2-yl CHCH1132 oxazol-2-yl CHCH1133 oxazol-4-yl CHCH1134 oxazol-5-yl CHCH1135 thiazol-2-yl CHCH1136 thiazol-4-yl CHCH1137 thiazol-5-yl CHCH1138 benzthiazol-2-yl CHCH1139 benzisothiazol-3-yl CHCH1140 isothiazol-3-yl CHCH1141 isothiazol-4-yl CHCH1142 isothiazol-5-yl CHCH1143 1,2,3-thiadiazol-4-yl CHCH__________________________________________________________________________
__________________________________________________________________________1144 1,2,4-thiadiazol-5-yl CHCH1145 1,3,4-thiadiazol-3-yl CHCH1146 2-furyl CH.sub.2 CH.sub.21147 5-nitro-2-furyl CH.sub.2 CH.sub.21148 5-chloro-2-furyl CH.sub.2 CH.sub.21149 2-(2'-furyl)-ethenyl CH.sub.2 CH.sub.21150 2-(5'-nitro-2'-furyl)ethenyl CH.sub.2 CH.sub.21151 3-furyl CH.sub.2 CH.sub.21152 5-nitro-3-furyl CH.sub.2 CH.sub.21153 5-chloro-3-furyl CH.sub.2 CH.sub.21154 2-(3'-furyl)ethenyl CH.sub.2 CH.sub.21155 2-(5'-nitro-3'-furyl)ethenyl CH.sub.2 CH.sub.21156 benzofuran-2-yl CH.sub.2 CH.sub.21157 benzofuran-3-yl CH.sub.2 CH.sub.21158 2-thienyl CH.sub.2 CH.sub.21159 5-nitro-2-thienyl CH.sub.2 CH.sub.21160 5-chloro-2-thienyl CH.sub.2 CH.sub.21161 2-(2'-thienyl)ethenyl CH.sub.2 CH.sub.21162 2-(5'-nitro-2'-thienyl)ethenyl CH.sub.2 CH.sub.21163 3-thienyl CH.sub.2 CH.sub.21164 5-nitro-3-thienyl CH.sub.2 CH.sub.21165 5-chloro-3-thienyl CH.sub.2 CH.sub.21166 2-(3'-thienyl)ethenyl CH.sub.2 CH.sub.21167 2-(5'-nitro-3'-thienyl)ethenyl CH.sub.2 CH.sub.21168 benzothien-2-yl CH.sub.2 CH.sub.21169 benzothien-3-yl CH.sub.2 CH.sub.21170 N-methyl-pyrrol-2-yl CH.sub.2 CH.sub.21171 N-methyl-pyrrol-3-yl CH.sub.2 CH.sub.21172 N-methyl-pyrazol-3-yl CH.sub.2 CH.sub.21173 N-methyl-pyrazol-4-yl CH.sub.2 CH.sub.21174 N-methyl-pyrazol-5-yl CH.sub.2 CH.sub.21175 N-methyl-imidazol-2-yl CH.sub.2 CH.sub.21176 N-methyl-imidazol-4-yl CH.sub.2 CH.sub.21177 N-methyl-imidazol-5-yl CH.sub.2 CH.sub.21178 1-methyl-1,2,3-triazol-4-yl CH.sub.2 CH.sub.21179 1-methyl-1,2,3-triazol-5-yl CH.sub.2 CH.sub.21180 1-methyl-1,2,4-triazol-3-yl CH.sub.2 CH.sub.21181 1-methyl-1,2,4-triazol-5-yl CH.sub.2 CH.sub.21182 1-methyl-tetrazol-5-yl CH.sub.2 CH.sub.21183 isoxazol-3-yl CH.sub.2 CH.sub.21184 isoxazol-4-yl CH.sub.2 CH.sub.21185 isoxazol-5-yl CH.sub.2 CH.sub.21186 benzisoxazol-3-yl CH.sub.2 CH.sub.21187 benzoxazol-2-yl CH.sub.2 CH.sub.21188 oxazol-2-yl CH.sub.2 CH.sub.21189 oxazol-4-yl CH.sub.2 CH.sub.21190 oxazol-5-yl CH.sub.2 CH.sub.21191 thiazol-2-yl CH.sub.2 CH.sub.21192 thiazol-4-yl CH.sub.2 CH.sub.21193 thiazol-5-yl CH.sub.2 CH.sub.21194 benzthiazol-2-yl CH.sub.2 CH.sub.21195 benzisothiazol-3-yl CH.sub.2 CH.sub.21196 isothiazol-3-yl CH.sub.2 CH.sub.21197 isothiazol-4-yl CH.sub.2 CH.sub.21198 isothiazol-5-yl CH.sub.2 CH.sub.21199 1,2,3-thiadiazol-4-yl CH.sub.2 CH.sub.21200 1,2,4-thiadiazol-5-yl CH.sub.2 CH.sub.21201 1,3,4-thiadiazol-3-yl CH.sub.2 CH.sub.21202 2-furyl CH.sub.2 O1203 5-nitro-2-furyl CH.sub.2 O1204 5-chloro-2-furyl CH.sub.2 O1205 2-(2'-furyl)-ethenyl CH.sub.2 O1206 2-(5'-nitro-2'-furyl)ethenyl CH.sub.2 O1207 3-furyl CH.sub.2 O1208 5-nitro-3-furyl CH.sub.2 O1209 5-chloro-3-furyl CH.sub.2 O1210 2-(3'-furyl)ethenyl CH.sub.2 O1211 2-(5'-nitro-3'-furanyl)ethenyl CH.sub.2 O1212 benzofuran-2-yl CH.sub.2 O1213 benzofuran-3-yl CH.sub.2 O1214 2-thienyl CH.sub.2 O1215 5-nitro-2-thienyl CH.sub.2 O1216 5-chloro-2-thienyl CH.sub.2 O1217 2-(2'-thienyl)ethenyl CH.sub.2 O1218 2-(5'-nitro-2'-thienyl)ethenyl CH.sub.2 O1219 3-thienyl CH.sub.2 O1220 5-nitro-3-thienyl CH.sub.2 O1221 5-chloro-3-thienyl CH.sub.2 O1222 2-(3'-thienyl)ethenyl CH.sub.2 O1223 2-(5'-nitro-3'-thienyl)ethenyl CH.sub.2 O1224 benzothien-2-yl CH.sub.2 O1225 benzothien-3-yl CH.sub.2 O1226 N-methyl-pyrrol-2-yl CH.sub.2 O1227 N-methyl-pyrrol-3-yl CH.sub.2 O1228 N-methyl-pyrazol-3-yl CH.sub.2 O1229 N-methy-pyrazol-4-yl CH.sub.2 O1230 N-methyl-pyrazol-5-yl CH.sub.2 O1231 N-methyl-imidazol-2-yl CH.sub.2 O1232 N-methyl-imidazol-4-yl CH.sub.2 O1233 N-methyl-imidazol-5-yl CH.sub.2 O1234 1-methyl-1,2,3-triazol-4-yl CH.sub.2 O1235 1-methyl-1,2,3-triazol-5-yl CH.sub.2 O1236 1-methyl-1,2,4-triazol-3-yl CH.sub.2 O1237 1-methyl-1,2,4-triazol-5-yl CH.sub.2 O1238 1-methyl-tetrazol-5-yl CH.sub.2 O1239 isoxazol-3-yl CH.sub.2 O1240 isoxazol-4-yl CH.sub.2 O1241 isoxazol-5-yl CH.sub.2 O1242 benzisoxazol-3-yl CH.sub.2 O1243 benzoxazol-2-yl CH.sub.2 O1244 oxazol-2-yl CH.sub.2 O1245 oxazol-4-yl CH.sub.2 O1246 oxazol-5-yl CH.sub.2 O1247 thiazol-2-yl CH.sub.2 O1248 thiazol-4-yl CH.sub.2 O1249 thiazol-5-yl CH.sub.2 O1250 benzthiasol-2-yl CH.sub.2 O1251 benzisothiazol-3-yl CH.sub.2 O1252 isothiazol-3-yl CH.sub.2 O1253 isothiazol-4-yl CH.sub.2 O1254 isothiazol-5-yl CH.sub.2 O1255 1,2,3-thiadiazol-4-yl CH.sub.2 O1256 1,2,4-thiadiazol-5-yl CH.sub.2 O1257 1,3,4-thiadiazol-3-yl CH.sub.2 O1258 2-furyl O1259 5-nitro-2-furyl O1260 5-chloro-2-furyl O1261 3-furyl O1262 5-nitro-3-furyl O1263 5-chloro-3-furyl O1264 benzofuran-2-yl O1265 benzofuran-3-yl O1266 2-thienyl O1267 5-nitro-2-thienyl O1268 5-chloro-2-thienyl O1269 3-thienyl O1270 5-nitro-3-thienyl O1271 5-chloro-3-thienyl O1272 benzothien-2-yl O1273 benzothien-3-yl O1274 N-methyl-pyrrol-2-yl O1275 N-methyl-pyrrol-3-yl O1276 N-methyl-pyrazol-3-yl O1277 N-methyl-pyrazol-4-yl O1278 N-methyl-pyrazol-5-yl O1279 N-methyl-imidazol-2-yl O1280 N-methyl-imidazol-4-yl O1281 N-methyl-imidazol-5-yl O1282 1-methyl-1,2,3-triazol-4-yl O1283 1-methyl-1,2,3-triazol-5-yl O1284 1-methyl-1,2,4-triazol-3-yl O1285 1-methyl-1,2,4-triazol-5-yl O1286 1-methyl-tetrazol-5-yl O1287 isoxazol-3-yl O1288 isoxazol-4-yl O1289 isoxazol-5-yl O1290 benzisoxazol-3-yl O1291 benzoxazol-2-yl O1292 oxazol-2-yl O1293 oxazol-4-yl O1294 oxazol-5-yl O1295 thiazol-2-yl O1296 thiazol-4-yl O1297 thiazol-5-yl O1298 benzthiazol-2-yl O1299 benzisothiazol-3-yl O1300 isothiazol-3-yl O1301 isothiazol-4-yl O1302 isothiazol-5-yl O1303 1,3-thiazolo[4,5-b]pyridin-2-yl O1304 2-furyl S1305 5-nitro-2-furyl S1306 5-chloro-2-furyl S1307 3-furyl S1308 5-nitro-3-furyl S1309 5-chloro-3-furyl S1310 benzofuran-2-yl S1311 benzofuran-3-yl S1312 2-thienyl S1313 5-nitro-2-thienyl S1314 5-chloro-2-thienyl S1315 3-thienyl S1316 5-nitro-3-thienyl S1317 5-chloro-3-thienyl S1318 benzothien-2-yl S1319 benzothien-3-yl S1320 N-methyl-pyrrol-2-yl S1321 N-methyl-pyrrol-3-yl S1322 N-methyl-pyrazol-3-yl S1323 N-methyl-pyrazol-4-yl S1324 N-methyl-pyrazol-5-yl S1325 N-methyl-imidazol-2-yl S1326 N-methyl-imidazol-4-yl S1327 N-methyl-imidazol-5-yl S1328 1-methyl-1,2,3-triazol-4-yl S1329 1-methyl-1,2,3-triazol-5-yl S1330 1-methyl-1,2,4-triazol-3-yl S1331 1-methyl-1,2,4-triazol-5-yl S1332 1-methyl-tetrazol-5-yl S1333 isoxazol-3-yl S1334 isoxazol-4-yl S1335 isoxazol-5-yl S1336 benzisoxazol-3-yl S1337 benzoxazol-2-yl S1338 oxazol-2-yl S1339 oxazol-4-yl S1340 oxazol-5-yl S1341 thiazol-2-yl S1342 oxazol-4-yl S1343 oxazol-5-yl S1344 thiazol-2-yl S1345 thiazol-4-yl S1346 thiazol-5-yl S1347 benzthiazol-2-yl S1348 benzisothiazol-3-yl S1349 isothiazol-3-yl S1350 isothiazol-4-yl S1351 isothiazol-5-yl S1352 1,3,-thiazolo[4,5-b]pyridin-2-yl S1353 2-furyl OCH.sub.21354 5-nitro-2-furyl OCH.sub.21355 5-chloro-2-furyl OCH.sub.21356 3-Furyl OCH.sub.21357 5-nitro-3-furyl OCH.sub.21358 5-chloro-3-furyl OCH.sub.21359 benzofuran-2-yl OCH.sub.21360 benzofuran-3-yl OCH.sub.21361 2-thienyl OCH.sub.21362 5-nitro-2-thienyl OCH.sub.21363 5-chloro-2-thienyl OCH.sub.21364 3-thienyl OCH.sub.21365 5-nitro-3-thienyl OCH.sub.21366 5-chloro-3-thienyl OCH.sub.21367 benzothien-2-yl OCH.sub.21368 benzothien-3-yl OCH.sub.21369 N-methyl-pyrrol-2-yl OCH.sub.21370 N-methyl-pyrrol-3-yl OCH.sub.21371 N-methyl-pyrazol-3-yl OCH.sub.21372 N-methyl-pyrazol-4-yl OCH.sub.21373 N-methyl-pyrazol-5-yl OCH.sub.21374 N-methyl-imidazol-2-yl OCH.sub.21375 N-methyl-imidazol-4-yl OCH.sub.21376 N-methyl-imidazol-5-yl OCH.sub.21377 1-methyl-1,2,3-triazol-4-yl OCH.sub.21378 1-methyl-1,2,3-triazol-5-yl OCH.sub.21379 1-methyl-1,2,4-triazol-3-yl OCH.sub.21380 1-methyl-1,2,4-triazol-5-yl OCH.sub.21381 1-methyl-tetrazol-5-yl OCH.sub.21382 isoxazol-3-yl OCH.sub.21383 isoxazol-4-yl OCH.sub.21384 isoxazol-5-yl OCH.sub.21385 benzisoxazol-3-yl OCH.sub.21386 benzoxazol-2-yl OCH.sub.21387 oxazol-2-yl OCH.sub.21389 oxazol-4-yl OCH.sub.21390 oxazol-5-yl OCH.sub.21391 thiazol-2-yl OCH.sub.21392 thiazol-4-yl OCH.sub.21393 thiazol-5-yl OCH.sub.21394 benzthiazol-2-yl OCH.sub.21395 benzisothiazol-3-yl OCH.sub.21396 isothiazol-3-yl OCH.sub.21397 isothiazol-4-yl OCH.sub.21398 isothiazol-5-yl OCH.sub.21399 2-furyl SCH.sub.21400 5-nitro-2-furyl SCH.sub.21401 5-chloro-2-furyl SCH.sub.21402 3-furyl SCH.sub.21403 5-nitro-3-furyl SCH.sub.21404 5-chloro-3-furyl SCH.sub.21405 benzofuran-2-yl SCH.sub.21406 benzofuran-3-yl SCH.sub.21407 2-thienyl SCH.sub.21408 5-nitro-2-thienyl SCH.sub.21409 5-chloro-2-thienyl SCH.sub.21410 3-thienyl SCH.sub.21411 5-nitro-3-thienyl SCH.sub.21412 5-chloro-3-thienyl SCH.sub.21413 benzothien-2-yl SCH.sub.21414 benzothien-3-yl SCH.sub.21415 N-methyl-pyrrol-2-yl SCH.sub.21416 N-methyl-pyrrol-3-yl SCH.sub.21417 N-methyl-pyrazol-3-yl SCH.sub.21418 N-methyl-pyrazol-4-yl SCH.sub.21419 N-methyl-pyrazol-5-yl SCH.sub.21420 N-methyl-imidazol-2-yl SCH.sub.21421 N-methyl-imidazol-4-yl SCH.sub.21422 N-methyl-imidazol-5-yl SCH.sub.21423 1-methyl-1,2,3-triazol-4-yl SCH.sub.21424 1-methyl-1,2,3-triazol-5-yl SCH.sub.21425 1-methyl-1,2,4-triazol-3-yl SCH.sub.21426 1-methyl-1,2,4-triazol-5-yl SCH.sub. 21427 1-methyl-tetrazol-5-yl SCH.sub.21428 isoxazol-3-yl SCH.sub.21429 isoxazol-4-yl SCH.sub.21430 isoxazol-5-yl SCH.sub.21431 benzisoxazol-3-yl SCH.sub.21432 benzoxazol-2-yl SCH.sub.21433 oxazol-2-yl SCH.sub.21434 oxazol-4-yl SCH.sub.21435 oxazol-5-yl SCH.sub.21436 thiazol-2-yl SCH.sub.21437 thiazol-4-yl SCH.sub.21438 thiazol-5-yl SCH.sub.21439 benzthiazol-2-yl SCH.sub.2 oil; .sup.1 H-NMR (CDCl.sub.3): .delta. = 3.78(3H), 4.58(2H), 5.83(1H), 6.63(1H), 7.1-7.9(8H)1440 benzisothiazol-3-yl SCH.sub.21441 isothiazol-3-yl SCH.sub.21442 isothiazol-4-yl SCH.sub.21443 isothiazol-5-yl SCH.sub.21444 1,2,3-thiadiazol-4-yl SCH.sub.21445 1,2,4-thiadiazol-5-yl SCH.sub.21446 1,3,4-thiadiazol-3-yl SCH.sub.21447 2-furyl COOCH.sub.21448 5-nitro-2-furyl COOCH.sub.21449 5-chloro-2-furyl COOCH.sub.21450 2-(2'-furyl)-ethenyl COOCH.sub.21451 2-(5'-nitro-2'furyl)ethenyl COOCH.sub.21452 3-furyl COOCH.sub.21453 5-nitro-3-furyl COOCH.sub.21454 5-chloro-3-furyl COOCH.sub.21455 2-(3'-furyl)ethenyl COOCH.sub.21456 2-(5'-nitro-3'-furanyl)ethenyl COOCH.sub.21457 benzofuran-2-yl COOCH.sub.21458 benzofuran-3-yl COOCH.sub.21459 2-thienyl COOCH.sub.21460 5-nitro-2-thienyl COOCH.sub.21461 5-chloro-2-thienyl COOCH.sub.21462 2-(2'-thienyl)ethenyl COOCH.sub.21463 2-(5'-nitro-2'-thienyl)ethenyl COOCH.sub.21464 3-thienyl COOCH.sub.21465 5-nitro-3-thienyl COOCH.sub.21466 5-chloro-3-thienyl COOCH.sub.21467 2-(3'-thienyl)ethenyl COOCH.sub.21468 2-(5'-nitro-3'-thienyl)ethenyl COOCH.sub.21469 benzothien-2-yl COOCH.sub.21470 benzothien-3-yl COOCH.sub.21471 N-methyl-pyrrol-2-yl COOCH.sub.21472 N-methyl-pyrrol-3-yl COOCH.sub.21473 N-methyl-pyrazol-3-yl COOCH.sub.21474 N-methyl-pyrazol-4-yl COOCH.sub.21475 N-methyl-pyrazol-5-yl COOCH.sub.21476 N-methyl-imidazol-2-yl COOCH.sub.21477 N-methyl-imidazol-4-yl COOCH.sub.21478 N-methyl-imidazol-5-yl COOCH.sub.21479 1-methyl-1,2,3-triazol-4-yl COOCH.sub.21480 1-methyl-1,2,3-triazol-5-yl COOCH.sub.21481 1-methyl-1,2,4-triazol-3-yl COOCH.sub.21482 1-methyl-1,2,4-triazol-5-yl COOCH.sub.21483 1-methyl-tetrazol-5-yl COOCH.sub.21484 isoxazol-3-yl COOCH.sub.21485 isoxazol-4-yl COOCH.sub.21486 isoxazol-5-yl COOCH.sub.21487 benzisoxazol-3-yl COOCH.sub.21488 benzoxazol-2-yl COOCH.sub.21489 oxazol-2-yl COOCH.sub.21490 oxazol-4-yl COOCH.sub.21491 oxazol-5-yl COOCH.sub.21492 thiazol-2-yl COOCH.sub.21493 thiazol-4-yl COOCH.sub.21494 thiazol-5-yl COOCH.sub.21495 benzthiasol-2-yl COOCH.sub.21496 benzisothiazol-3-yl COOCH.sub.21497 isothiazol-3-yl COOCH.sub.21498 isothioazol-4-yl COOCH.sub.21499 isothiazol-5-yl COOCH.sub.21500 1,2,3-thiadiazol-4-yl COOCH.sub.21501 1,2,4-thiadiazol-5-yl COOCH.sub.21502 1,3,4-thiadiazol-3-yl COOCH.sub.21503 2-furyl NHCOO1504 5-nitro-2-furyl NHCOO1505 5-chloro-2-furyl NHCOO1506 3-furyl NHCOO1507 5-nitro-3-furyl NHCOO1508 5-chloro-3-furyl NHCOO1509 benzofuran-2-yl NHCOO1510 benzofuran-3-yl NHCOO1511 2-thienyl NHCOO1512 5-nitro-2-thienyl NHCOO1513 5-chloro-2-thienyl NHCOO1514 3-thienyl NHCOO1515 5-nitro-3-thienyl NHCOO1516 5-chloro-3-thienyl NHCOO1517 benzothien-2-yl NHCOO1518 benzothien-3-yl NHCOO1519 N-methyl-pyrrol-2-yl NHCOO1520 N-methyl-pyrrol-3-yl NHCOO1521 N-methyl-pyrazol-3-yl NHCOO1522 N-methyl-pyrazol-4-yl NHCOO1523 N-methyl-pyrazol-5-yl NHCOO1524 N-methyl-imidazol-4-yl NHCOO1526 N-methyl-imidazol-5-yl NHCOO1527 1-methyl-1,2,3-triazol-4-yl NHCOO1528 1-methyl-1,2,3-triazol-5-yl NHCOO1529 1-methyl-1,2,4-triazol-3-yl NHCOO1530 1-methyl-1,2,4-triazol-5-yl NHCOO1531 1-methyl-tetrazol-5-yl NHCOO1532 isoxazol-3-yl NHCOO1533 isoxazol-4-yl NHCOO1534 isoxazol-5-yl NHCOO1535 benzisoxazol-3-yl NHCOO1536 benzoxazol-2-yl NHCOO1537 oxazol-2-yl NHCOO1538 oxazol-4-yl NHCOO1539 oxazol-5-yl NHCOO1540 thiazol-2-yl NHCOO1541 thiazol-4-yl NHCOO1542 thiazol-5-yl NHCOO1543 benzthiazol-2-yl NHCOO1544 benzisothiazol-3-yl NHCOO1545 isothiazol-3-yl NHCOO1546 isothiazol-4-yl NHCOO1547 isothiazol-5-yl NHCOO1548 2-furyl COO1549 5-nitro-2-furyl COO1550 5-chloro-2-furyl COO1551 2-(2'-furyl)-ethenyl COO1552 2-(5'-nitro-2'-furyl)ethenyl COO1553 3-furyl COO1554 5-nitro-3-furyl COO1555 5-chloro-3-furyl COO1556 2-(3'-furyl)ethenyl COO1557 2-(5'-nitro-3'-furanyl)ethenyl COO1558 benzofuran-2-yl COO1559 benzofuran-3-yl COO1560 2-thienyl COO1561 5-nitro-2-thienyl COO1562 5-chloro-2-thienyl COO1563 2-(2'-thienyl)ethenyl COO1564 2-(5'-nitro-2'-thienyl)ethenyl COO1565 3-thienyl COO1566 5-nitro-3-thienyl COO1567 5-chloro-3-thienyl COO1568 2-(3'-thienyl)ethenyl COO1569 2-(5'-nitro-3'-thienyl)ethenyl COO1570 benzothien-2-yl COO1571 benzothien-3-yl COO1572 N-methyl-pyrrol-2-yl COO1573 N-methyl-pyrrol-3-yl COO1574 N-methyl-pyrazol-3-yl COO1575 N-methyl-pyrazol-4-yl COO1576 N-methyl-pyrazol-5-yl COO1577 N-methyl-imidazol-2-yl COO1578 N-methyl-imidazol-4-yl COO1579 N-methyl-imidazol-5-yl COO1580 1-methyl-1,2,3-triazol-4-yl COO1581 1-methyl-1,2,3-triazol-5-yl COO1582 1-methyl-1,2,4-triazol-3-yl COO1583 1-methyl-1,2,4-triazol-5-yl COO1584 1-methyl-tetrazol-5-yl COO1585 isoxazol-3-yl COO1586 isoxazol-4-yl COO1587 isoxazol-5-yl COO1588 benzisoxazol-3-yl COO1589 benzoxazol-2-yl COO1590 oxazol-2-yl COO1591 oxazol-4-yl COO1592 oxazol-5-yl COO1593 thiazol-2-yl COO1594 thiazol-4-yl COO1595 thiazol-5-yl COO1596 benzthiazol-2-yl COO1597 benzisothiazol-3-yl COO1598 isothiazol-3-yl COO1599 isothioazol-4-yl COO1600 isothiazol-5-yl COO1601 1,2,3-isodiazol-4-yl COO1602 1,2,4-thiadiazol-5-yl CO O1603 1,3,4-thiadiazol-3-yl COO1604 2-furyl OCO1605 5-nitro-2-furyl OCO1606 5-chloro-2-furyl OCO1607 3-furyl OCO1608 5-nitro-3-furyl OCO1609 5-chloro-3-furyl OCO1610 benzofuran-2-yl OCO1611 benzofuran-3-yl OCO1612 2-thienyl OCO1613 5-nitro-2-thienyl OCO1614 5-chloro-2-thienyl OCO1615 3-thienyl OCO1616 5-nitro-3-thienyl OCO1617 5-chloro-3-thienyl OCO1618 benzothien-2-yl OCO1619 benzothien-3-yl OCO1620 N-methyl-pyrrol-2-yl OCO1621 N-methyl-pyrrol-3-yl OCO1622 N-methyl-pyrazol-3-yl OCO1623 N-methyl-pyrazol-4-yl OCO1625 N-methyl-imidazol-2-yl OCO1626 N-methyl-imidazol-4-yl OCO1627 N-methyl-imidazol-5-yl OCO1628 1-methyl-1,2,3-triazol-4-yl OCO1629 1-methyl-1,2,3-triazol-5-yl OCO1630 1-methyl-1,2,4-triazol-3-yl OCO1631 1-methyl-1,2,4-triazol-5-yl OCO1632 1-methyl-tetrazol-5-yl OCO1633 isoxazol-3-yl OCO1634 isoxazol-4-yl OCO1635 isoxazol-5-yl OCO1636 benzoisoxazol-3-yl OCO1637 benzoxazol-2-yl OCO1638 oxazol-2-yl OCO1639 oxazol-4-yl OCO1640 oxazol-5-yl OCO1641 thiazol-2-yl OCO1642 thiazol-4-yl OCO1643 thiazol-5-yl OCO1644 benzthiazol-2-yl OCO1645 benzisothiazol-3-yl OCO1646 isothiazol-3-yl OCO1647 isothiazol-4-yl OCO1648 isothiazol-5-yl OCO1649 1,2,3-thiadiazol-4-yl OCO1650 1,2,4-thiadiazol-5-yl OCO1651 1,3,4-thiadiazol-3-yl OCO1652 6-chloro-benzothiazol-2-yl SCH.sub.2 oil; .sup.1 H-NHR (CDCl.sub.3): .delta. = 3.78(3H), 4.53(2H), 5.84(1H), 6.62(1H), 7.1-7.8(7H)__________________________________________________________________________
Generally speaking, 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 sugar cane,
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 90wt % 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, for example 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. 460 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. 632 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. 649 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. 773 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. 866 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 sulfite 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. 866 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. 460 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. 632 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. 649 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-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole,
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-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide,
5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,
2-thiocyanatomethylthiobenzothiazole,
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,
3 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-carboximide,
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-dimethylmorpholine,
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-triazol-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 EXAMPLES
As comparative active ingredient, methyl .alpha.-phenylacrylate (A) disclosed in C.A. Reg. No. 1865-29-8 was used.
USE EXAMPLE 1
Action on Pyricularia oryzae (Protective)
Leaves of pot-grown 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 extent of fungus spread was determined after 6 days.
The results show that active ingredients 460, 632, 649, 773 and 866, applied as 0.05 wt % spray liquors, had a better fungicidal action (95%) than prior art active ingredient A (60%).
USE EXAMPLE 2
Action on Pyrenophora teres
Barley seedlings of the "Igri" variety were sprayed to runoff at the two-leaf stage with aqueous suspensions consisting (dry basis) of 80% of active ingredient and 20% of emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres, and set up for 48 hours in a high-humidity climatic cabinet at 18.degree. C. The plants were then cultivated for a further 5 days in the greenhouse at 20.degree. to 22.degree. C. and a relative humidity of 70.degree. C. The extent of fungus spread was then assessed.
The results show that active ingredients 649 and 1439, applied as 0.05% spray liquors, had a better fungicidal action (90%) than prior art comparative compound A (0%).
USE EXAMPLE 3
Action on Wheat Mildew
Leaves of pot-grown wheat seedlings of the "Kanzler" variety were sprayed to runoff with aqueous liquors consisting (dry basis) of 80% of active ingredient and 20% of emulsifier, and dusted, 24 hours after the sprayed-on layer had dried, with spores or wheat mildew (Erisyphe graminis var. tritici). The plants were set up in the greenhouse at from 20.degree. to 22.degree. C. and a relative humidity of from 75 to 80%. The extent of mildew spread was determined after 7 days.
The results show that active ingredients 632 and 649, applied as 0.025% spray liquors, had a better fungicidal action (90%) than prior art comparative agent A (40%).

.alpha.-arylacrylates and fungicides containing these compounds

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US Referenced Citations (1)

Non-Patent Literature Citations (4)

Entry
C A 85(21) 159105g 1976.
C A 82(13) 85829l 1975.
Journal of The American Chemical Society, vol. 98, No. 12, Jun. 1976, pp. 3555-3564.
C. A. S. Registry Handbook, 1979, Supplement, pp. 1557 . RH1557, RN-70932-72-8.