N-(arylpropyl)-azolylureas, and fungicides containing these compounds

N-(Arylpropyl)-azolylureas of the formula ##STR1## where R is alkyl, X is hydrogen, halogen, nitro, cyano, trifluoromethyl, alkyl, alkoxy, alkylthio, phenyl or phenoxy, m is an integer from 1 to 4, Y is CH or N, R.sup.1 is alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl or cycloalkylalkyl or an unsubstituted or substituted phenyl or benzyl radical, and R.sup.2 and R.sup.3 are each hydrogen or alkyl, and fungicides which contain these compounds.

The present invention relates to novel N-(arylpropyl)-azolylureas, 
processes for their preparation, and fungicides which contain these 
compounds as active ingredients. 
It has been disclosed that N-trichloromethylthiotetrahydrophthalimide and 
N-trichloromethylthiophthalimide can be used as fungicides in agriculture 
as well as in fruit cultivation and horticulture (Chemical Week, 1972, 
June 21, pages 46 and 63). However, the conventional agents can be used 
only before infection, and their actions do not meet practical 
requirements at low application rates. 
We have found that N-(arylpropyl)-azolylureas of the formula 
##STR2## 
where R is alkyl of 1 to 4 carbon atoms, X is hydrogen, halogen, nitro, 
cyano, trifluoromethyl or alkyl, alkoxy or alkylthio, each of which is of 
1 to 6 carbon atoms, or phenyl or phenoxy, m is an integer from 1 to 4, 
the individual groups X being identical or different when m is greater 
than 1, Y is CH or N, R.sup.1 is alkyl, alkenyl, alkoxyalkyl, 
alkylthioalkyl, cycloalkyl or cycloalkylalkyl, each of not more than 12 
carbon atoms, or is phenyl or benzyl, each of which is unsubstituted or 
substituted by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, 
trifluoromethyl, nitro or cyano, and R.sup.2 and R.sup.3 are identical or 
different and are each hydrogen or alkyl of 1 to 5 carbon atoms, are very 
effective against harmful fungi. 
The novel compounds of the formula I contain chiral centers and are 
generally obtained in the form of racemates or diastereomer mixtures. For 
some of the novel compounds, the diastereomers can be separated, for 
example by column chromatography, or can be isolated in pure form on the 
basis of solubility differences. Pure enantiomers can be obtained from 
such pure diastereomers by a conventional method. The mixtures and the 
pure compounds are embraced by the present invention. When the novel 
compounds are used as fungicides, both the pure diastereomers or 
enantiomers and mixtures of these obtained in the synthesis are suitable, 
the mixtures preferably being used. 
X is preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, 
trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 
sec.-butyl, tert.-butyl, methoxy, ethoxy, methylthio, phenyl or phenoxy. 
In formula I, suitable radicals R.sup.1 are methyl, ethyl, n-propyl, 
n-butyl, isobutyl, sec.-butyl, n-pentyl, 3-methylbut-1-yl, 
2-methylbut-1-yl, 3-pentyl, n-hexyl, 3,3-dimethylbut-1-yl, 
2,2,3-trimethylprop-1-yl, n-heptyl, n-octyl, 2,4,4-trimethylpentyl, 
2-ethylhexyl, n-nonyl, 3,5,5-trimethylhexyl, 2-isopropyl-5-methylhexyl, 
2-isopropyl-3-methylhexyl, n-decyl, 3,7-dimethyloctyl, dodecyl, 
cyclopropylmethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 
4-methylcyclohexyl, 4-tert.-butylcyclohexyl, 4-methoxycyclohexyl, 
2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 
2-hexyloxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 
3-butoxypropyl, 3-hexyloxypropyl, 2-methylthioethyl, 2-ethylthioethyl, 
2-propylthioethyl, 2-butylthioethyl, 3-methylthiopropyl, 
3-ethylthiopropyl, 3-propylthiopropyl, allyl, 2-methylallyl, 
but-2-en-1-yl, pent-2-en-1-yl, phenyl, 4-fluorophenyl, 4-chlorophenyl, 
2,4-dichlorophenyl, 3,4-dichlorophenyl, 4-bromophenyl, 4-methylphenyl, 
4-tert.-butylphenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-trifluoromethyl, 
4-cyanophenyl, benzyl, 4-fluorobenzyl, 4-chlorobenzyl, 3,4-dichlorobenzyl, 
2,4-dichlorobenzyl, 4-bromobenzyl, 4-methylbenzyl, 4-tert.-butylbenzyl, 
4-methoxybenzyl, 3- and 4-trifluoromethylbenzyl and 4-ethoxybenzyl. 
R.sup.2 and R.sup.3 are each preferably hydrogen, methyl, ethyl, n-propyl 
or isopropyl, R is methyl or ethyl, Y is nitrogen or CH and m is an 
integer from 1 to 4. 
The compounds of the formula I can be prepared by a method in which a 
carbamyl chloride of the formula 
##STR3## 
where R, R.sup.1 and X have the above meanings, is reacted with 
(a) an azole of the formula III 
##STR4## 
where R.sup.2, R.sup.3 and Y have the above meanings, or 
(b) a metal derivative of this, of the formula IV 
##STR5## 
where R.sup.2, R.sup.3 and Y have the above meanings and Me is lithium, 
sodium, potassium or an equivalent of calcium, or 
(c) a silyl derivative of this, of the formula V 
##STR6## 
where R.sup.2, R.sup.3 and Y have the above meanings. 
Reaction (a) is carried out in the presence or absence of a solvent or 
diluent and with or without the addition of an inorganic or organic base 
and of a reaction accelerator, at from 10.degree. to 120.degree. C. 
Examples of preferably used solvents or diluents which are inert to the 
reactants are aliphatic or aromatic hydrocarbons and halohydrocarbons, 
such as n-pentane, cyclohexane, methylene chloride, 1,1,1-trichloroethane, 
benzene, toluene, xylene or chlorobenzene, aliphatic ketones, such as 
acetone, methyl ethyl ketone or diethyl ketone, ethers, such as diethyl 
ether, methyl tert.-butyl ether, dimethoxyethane, tetrahydrofuran or 
dioxane, esters, such as ethyl acetate, nitriles, such as acetonitrile, 
and amides, such as dimethylformamide, dimethylacetamide and 
N-methylpyrrolidone, and mixtures of these. 
Examples of suitable bases which, if required, may also be used in the 
reaction as acid acceptors are alkali metal hydroxides, such as lithium 
hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, 
alkali metal carbonates, such as sodium carbonate, potassium carbonate, 
sodium bicarbonate or potassium bicarbonate, and amines, such as 
triethylamine, tripropylamine, N-methylpyrrolidine, N-methylpiperidine, 
N,N-dimethylcyclohexylamine, N,N'-tetramethylethylenediamine, 
N,N-dimethylaniline, N,N-diethylaniline, pyridine or 
4-dimethylaminopyridine. Other conventional bases may also be used. 
Preferred reaction accelerators are metal halides, such as sodium iodide or 
potassium iodide, quaternary ammonium salts, such as tetrabutylammonium 
chloride, bromide or iodide or benzyltriethylammonium chloride or bromide, 
and crown ethers, such as 12-crown-4, 15-crown-5, 18-crown-6 or 
dibenzo-18-crown-6. 
Reactions (b) and (c) are carried out in the presence or absence of a 
solvent or diluent, at from 0.degree. to 140.degree. C., preferably from 
0.degree. to 100.degree. C. Solvents which can be used for these reactions 
are those which are suitable for version (a) of the process. 
Compounds of the formula I can furthermore be prepared by reacting a 
secondary amine of the formula VI 
##STR7## 
where R, R.sup.1 and X have the above meanings, with a carbonyl-bisazole 
of the formula VII 
##STR8## 
where R.sup.2, R.sup.3 and Y have the above meanings, in the presence or 
absence of a solvent or diluent and with or without the addition of a 
reaction accelerator. 
Examples of suitable solvents or diluents for this purpose are diethyl 
ether, 1,2-dimethoxyethane, dipropyl ether, dibutyl ether, methyl 
tert.-butyl ether, tetrahydrofuran, dimethoxyethane, anisole, n-pentane, 
n-hexane, n-heptane, n-octane, isooctane, cyclohexane, toluene, 
chlorobenzene, xylenes, acetonitrile, ethyl acetate, dimethylformamide, 
N-methylpyrrolidone, acetone and methyl ethyl ketone. 
Examples of suitable reaction accelerators are 4-dimethylaminopyridine and 
4-pyrrolidinopyridine. 
The starting materials of the formula II can readily be prepared by a 
conventional method, for example by reacting an amine of the formula VI 
with phosgene (Houben-Weyl-Muller, Methoden der organischen Chemie, Volume 
8, pages 115-118, Georg Thieme Verlag, Stuttgart, 1952). 
The secondary amines of the formula VI are obtained by reacting a known 
amine of the formula R.sup.1 --NH.sub.2, where R.sup.1 has the above 
meanings, with an arylpropyl halide (cf. European Pat. No. 9077) of the 
formula VIII or with an aldehyde of the formula IX 
##STR9## 
where R, X and m have the above meanings and Z is chlorine or bromine, in 
the presence or absence of a strong inorganic or organic base, of a 
solvent or diluent and of a hydrogenating compound and/or a catalyst.

The Examples which follow illustrate the preparation of the compounds of 
the formula I. 
EXAMPLE 1 
(a) 204 g of 3-(4'-tert.-butylphenyl)-2-methylpropionaldehyde were added 
dropwise to a solution of 71 g (1 mole) of n-butylamine in 800 ml of 
ethanol at 25.degree. C., and the mixture was stirred for 36 hours at 
25.degree. C. Thereafter, 87 g (2.28 moles) of sodium borohydride were 
added, a little at a time, to the mixture, and stirring was continued for 
a further 4 hours at 78.degree. C. The mixture was cooled, diluted with 
1.5 l of water and extracted with three times 300 ml of methylene 
chloride, and the combined extracts were washed with 300 ml of water, 
dried and distilled. 
170 g of N-butyl-N-(1-(4'-tert.-butylphenyl)-2-methylprop-3-yl)-amine of 
boiling point 125.degree. C./0.4 mbar were obtained. 
(b) 51.2 g (0.196 mole) of 
N-butyl-N-(1-(4'-tert.-butylphenyl)-2-methylprop-3-yl)-amine were added 
dropwise to a solution of phosgene in 200 ml of dry ethyl acetate, the 
solution being saturated at 10.degree. C. The mixture was stirred for 6 
hours at 50.degree. C., phosgene being passed in, and then cooled to 
20.degree. C. and evaporated down under reduced pressure, in the final 
stages at 60.degree. C. and under 0.4 mbar. 
61 g of N-(1-4'-tert.-butylphenyl)-2-methylprop-3-yl)-N-butylcarbamyl 
chloride were obtained as a colorless oil, which was directly reacted 
further. 
(c) 20.4 g (0.3 mole) of imidazole were added, a little at a time, to a 
solution of 32.4 g (0.1 mole) of 
N-(1-(4'-tert.-butylphenyl)-2-methylprop-3-yl)-N-butylcarbamyl chloride in 
250 ml of dry tetrahydrofuran, and the mixture was stirred for 6 hours at 
70.degree. C. Thereafter, the mixture was cooled to 20.degree. C., the 
precipitate formed was filtered off under suction, the filtrate was 
evaporated down under reduced pressure, the residue was taken up in 200 ml 
of methylene chloride, and the solution was washed with three times 80 ml 
of water, dried and evaporated down. 
29.2 g of 
1-(N-(1-(4'-tert.-butylphenyl)-2-methylprop-3-yl)-N-butylcarbamyl)-imidazo 
le were obtained as a colorless resin (Compound No. 1). IR (film) 
[cm.sup.-1 ]: 2961, 2933, 2872, 1694, 1464, 1421, 1365, 1286, 1272, 1231, 
1100, 1066, 1020, 750, 658. 
EXAMPLE 2 
14 g (0.0433 mole) of 
N-(1-(4'-tert.-butylphenyl)-2-methylprop-3-yl)-N-butylcarbamyl chloride 
were added dropwise to a suspension of 5.5 g (0.06 mole) of sodium 
1,2,4-triazolide in 120 ml of dry tetrahydrofuran at 20.degree. C., and 
the mixture was stirred for 6 hours at 65.degree. C. Thereafter, the 
mixture was cooled to 20.degree. C., the precipitate was filtered off 
under suction, the filtrate was evaporated down, the residue was dissolved 
in 150 ml of methylene chloride, and the solution was washed with three 
times 50 ml of water, dried and evaporated down. 13.3 g of 
1-(N-(1-(4'-tert.-butylphenyl)-2-methylprop-3-yl)-N-butylcarbamyl)-1,2,4-t 
riazole were obtained as a colorless resin (Compound No. 2). IR (film) 
[cm.sup.-1 ]: 2961, 2931, 2871, 1699, 1508, 1464, 1426, 1379, 1364, 1275, 
1210, 1192, 1136, 1001, 671. 
The compounds listed in the Table below can be prepared in a similar 
manner: 
__________________________________________________________________________ 
Compound M.p. [.degree.C.] 
no. X R R.sup.1 Y R.sup.2 
R.sup.3 
IR (film) [cm.sup.-1 
__________________________________________________________________________ 
] 
3 H CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H 
4 H CH.sub.3 
n-C.sub.4 H.sub.9 
N H H 
5 H C.sub.2 H.sub.5 
n-C.sub.4 H.sub.9 
CH H H 
6 H C.sub.2 H.sub.5 
n-C.sub.4 H.sub.9 
N H H 
7 H CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H 
8 H CH.sub.3 
n-C.sub.6 H.sub.13 
N H H 
9 H CH.sub.3 
cyclopropylmethyl 
CH H H 
10 H CH.sub.3 
cyclopropylmethyl 
N H H 
11 H CH.sub.3 
--(CH.sub.2).sub.2 OC.sub.2 H.sub.5 
CH H H 
12 H CH.sub.3 
--(CH.sub.2).sub.2 OC.sub.2 H.sub.5 
N H H 
13 4-F CH.sub.3 
n-C.sub.3 H.sub.7 
CH H H 2963, 1692, 1509, 
1462, 1421, 1298, 
1276, 1242, 1221, 
1099, 1013, 760, 656 
14 4-F CH.sub.3 
n-C.sub.3 H.sub.7 
N H H 2966, 1699, 1510, 1427, 
1220, 1001, 671 
15 4-F CH.sub.3 
--(CH.sub.2).sub.3 OC.sub.4 H.sub.5 --n 
CH H H 
16 4-F CH.sub.3 
--(CH.sub.2).sub.3 O--C.sub.4 H.sub.5 --n 
N H H 
17 4-F CH.sub.3 
--C.sub.6 H.sub.5 
CH H H 
18 4-F CH.sub.3 
--C.sub.6 H.sub.5 
N H H 
19 4-Cl CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H n.sub.D.sup.22 1.5342 
20 4-Cl CH.sub.3 
n-C.sub.6 H.sub.13 
N H H n.sub.D.sup.22 1.5279 
21 4-Cl CH.sub.3 
--(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub 
.3 CH H H 
22 4-Cl CH.sub.3 
--(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub 
.3 N H H 
23 4-Br CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H 
24 4-Br CH.sub.3 
n-C.sub.4 H.sub.9 
N H H 
25 4-CH.sub.3 O-- 
CH.sub.3 
n-C.sub.3 H.sub.7 
CH H H 2962, 2933, 1692, 
1611, 1512, 1462, 
1421, 1299, 1275, 
1221, 1178, 1034, 
754 
26 4-CH.sub.3 O-- 
CH.sub.3 
n-C.sub.3 H.sub.7 
N H H 2963, 1698, 1512, 1426, 
1276, 1247, 1179, 1001 
27 4-C.sub.2 H.sub.5 O-- 
CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H 
28 4-C.sub.2 H.sub.5 O-- 
CH.sub.3 
n-C.sub.6 H.sub.13 
N H H 
29 4-C.sub.6 H.sub.13 O-- 
CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H 
30 4-C.sub.6 H.sub.13 O-- 
CH.sub.3 
n-C.sub.4 H.sub.9 
N H H 
31 4-CH.sub.3 
CH.sub.3 
n-C.sub.3 H.sub.7 
CH H H 2963, 2930, 1693, 
1515, 1461, 1421, 
1380, 1364, 1298, 
1275, 1220, 1100, 
1015, 754 
32 4-CH.sub.3 
CH.sub.3 
n-C.sub.3 H.sub.7 
N H H 2965, 1699, 1428, 1381, 
1275, 1138, 1001, 748 
33 4-C.sub.2 H.sub.5 
CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H 
34 4-C.sub.2 H.sub.5 
CH.sub.3 
n-C.sub.5 H.sub.13 
N H H 
35 4-isoC.sub.3 H.sub.7 
CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H 
36 4-isoC.sub.3 H.sub.7 
CH.sub.3 
n-C.sub.4 H.sub.9 
N H H 
37 4-isoC.sub.3 H.sub.7 
CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H 
38 4-isoC.sub.3 H.sub.7 
CH.sub.3 
n-C.sub.6 H.sub.13 
N H H 
39 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
CH.sub.3 CH H H 70-72 
40 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
CH.sub.3 CH H isoC.sub.3 H.sub.7 
2965, 2931, 2870, 
1701, 1510, 1476, 
1461, 1364, 1244, 
1231, 1108 
41 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
CH.sub.3 N H H 2961, 2869, 1704, 
1508, 1478, 1406, 
1380, 1364, 1275, 
1197, 1131, 998, 
746, 671 
42 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
C.sub.2 H.sub.5 CH H H 2963, 1695, 1461, 
1422, 1328, 1249, 
1220, 1018, 900, 758 
43 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
C.sub.2 H.sub.5 N H H 
44 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
n-C.sub.3 H.sub.7 
CH H H 2963, 2873, 1693, 
1462, 1420, 1365, 
1272, 1242, 1100, 
1065, 1017, 755, 658 
45 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
n-C.sub.3 H.sub.7 
CH H iso-C.sub.3 H.sub.7 
2964, 2872, 1693, 
1511, 1460, 1417, 
1380, 1363, 1346, 
1269, 1109, 1096, 
1070 
46 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
n-C.sub.3 H.sub.7 
N H H 2963, 2873, 1700, 
1509, 1462, 1426, 
1380, 1364, 1274, 
1244, 1211, 1001, 671 
47 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
n-C.sub.4 H.sub.9 
CH H isoC.sub.3 H.sub.7 
2962, 2872, 1695, 
1460, 1418, 1379, 
1363, 1288, 1270, 
1109, 1096, 1070, 
718 
48 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
--(CH.sub.2).sub.2 CH(CH.sub.3).sub.2 
CH H H 
49 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
--(CH.sub.2).sub.2 CH(CH.sub.3).sub.2 
N H H 
50 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H n.sub.D.sup.23 1.5205 
51 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
n-C.sub.6 H.sub.13 
N H H 
52 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
--CH.sub.2 CH(C.sub.2 H.sub.5)(CH.sub.2).sub.3 
CH.sub.3 CH H H 
53 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
--CH.sub.2 CH(C.sub.2 H.sub.5)(CH.sub.2).sub.3 
CH.sub.3 N H H 
54 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
n-C.sub.7 H.sub.15 
CH H H 
55 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
n-C.sub.7 H.sub.15 
N H H 
56 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
4-Cl-C.sub.6 H.sub.4 -- 
CH H H 1701, 1494, 1416, 
1394, 1287, 1251, 
1095, 1015, 846, 750, 
735, 654, 570 
57 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
4-Cl-C.sub.6 H.sub.4 -- 
CH H isoC.sub.3 H.sub.7 
1701, 1493, 1414, 
1393, 1289, 1269, 
1095, 1070, 1016, 
838, 759, 738, 723,608 
58 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
4-Cl--C.sub.6 H.sub.4 -- 
N H H 1708, 1509, 1493, 
1458, 1440, 1420, 
1400, 1380, 1281, 
1092, 1014, 990 
59 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
cyclohexyl CH H H 
60 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
cyclohexyl N H H 2933, 1700, 1508, 1421, 
1273, 1003, 731, 671 
61 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
4-methylcyclohexyl 
CH H H 2858, 1695, 1410, 1240, 
1100, 1019, 732, 657 
62 4-tert.-C.sub.4 H.sub.9 
CH.sub.3 
4-methylcyclohexyl 
N H H 
63 4-C(CH.sub.3).sub.2 C.sub.2 H.sub.5 
CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H n.sub.D.sup.22 1.5168 
64 4-C(CH.sub.3).sub.2 C.sub.2 H.sub.5 
CH.sub.3 
n-C.sub.6 H.sub.13 
N H H n.sub.D.sup.22 1.5111 
65 4-CF.sub.3 
CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H 
66 4-CF.sub.3 
CH.sub.3 
n-C.sub.6 H.sub.13 
N H H 
67 4-isoC.sub.3 H.sub.7 
CH.sub.3 
CH.sub.3 CH H H 2959, 2927, 1696, 
1512, 1484, 1459, 
1402, 1382, 1282, 
1217, 1099, 1009, 
754, 656 
68 4-iso-C.sub.3 H.sub.7 
CH.sub.3 
CH.sub.3 N H H 2959, 2927, 1703, 
1510, 1479, 1406, 
1381, 1363, 1276, 
1198, 1131, 998, 671 
69 2,4-Cl.sub.2 
CH n-C.sub.3 H.sub.7 
CH H H 2963, 2933, 1693, 
1473, 1420, 1382, 
1299, 1275, 1242, 
1103, 1066, 1015, 
744, 657 
70 2,4-Cl.sub.2 
CH.sub.3 
n-C.sub.3 H.sub.7 
N H H 2965, 1698, 1474, 
1426, 1382, 1276, 
1244, 1105, 1001, 746, 
670 
71 2,4-Cl.sub.2 
CH.sub.3 
--CH.sub.2 --CH.dbd.CH.sub.2 
CH H H 
72 2,4-Cl.sub.2 
CH.sub.3 
--CH.sub.2 --CH.dbd.CH.sub.2 
N H H 
73 2,4-Cl.sub.2 
CH.sub.3 
--CH.sub.2 --CH.dbd.CH--CH.sub.3 
CH H H 
74 2,4-Cl.sub.2 
CH.sub.3 
--CH.sub.2 --CH.dbd.CH--CH.sub.3 
N H H 
75 2,4-Cl.sub.2 
CH.sub.3 
--CH.sub.2 --CH.dbd.CH--C.sub.3 H.sub.6 
CH H H 
76 2,4-Cl.sub.2 
CH.sub.3 
iso-C.sub.4 H.sub.9 
CH H H 2960, 1693, 1472, 
1419, 1385, 1277, 
1244, 1103, 1065, 
1018, 745, 657 
77 2,4-Cl.sub.2 
CH.sub.3 
iso-C.sub.4 H.sub.9 
N H H 2961, 1698, 1473, 1381, 
1275, 1003, 670 
78 2,4-Cl.sub.2 
CH.sub.3 
n-C.sub.12 H.sub.25 
CH H H 2953, 2924, 2853, 
1695, 1472, 1420, 
1379, 1299, 1274, 
1240, 1220, 1103, 
1065, 744 
79 2,4-Cl.sub.2 
CH.sub.3 
n-C.sub.12 H.sub.25 
N H H 2924, 1699, 1472, 1426, 
1275, 1000, 744, 670 
80 2,4-Cl.sub.2 
CH.sub.3 
cyclohexyl CH H H 2933, 1694, 1474, 
1409, 1377, 1303, 
1240, 1103, 1020, 746 
81 2,4-Cl.sub.2 
CH.sub.3 
cyclohexyl N H H 65-67 
82 H n-C.sub.3 H.sub.7 
n-C.sub.6 H.sub.13 
CH H H n.sub.D.sup.25 1.5321 
83 H n-C.sub.3 H.sub.7 
n-C.sub.6 H.sub.13 
N H H n.sub.D.sup.25 1.5136 
84 H n-C.sub. 4 H.sub.9 
n-C.sub.4 H.sub.9 
CH H H n.sub.D.sup.22 1.5224 
85 H n-C.sub.4 H.sub.9 
n-C.sub.4 H.sub.9 
N H H n.sub.D.sup.22 1.5172 
86 H n-C.sub.4 H.sub.9 
n-C.sub.6 H.sub.13 
CH H H n.sub.D.sup.20 1.5178 
87 H n-C.sub.4 H.sub.9 
n-C.sub.6 H.sub.13 
N H H n.sub.D.sup.20 1.5125 
88 2-F CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H n.sub.D.sup.22 1.5262 
89 2-F CH.sub.3 
n-C.sub.4 H.sub.9 
NH H H n.sub.D.sup.22 1.5180 
90 2-F CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H n.sub.D.sup.22 1.5192 
91 4-Cl CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H n.sub.D.sup.23 1.5428 
92 4-CH.sub.3 
CH.sub.3 
cyclohexyl CH H H 2930, 1694, 1515, 
1409, 1376, 1241, 
1100, 1020, 757 
93 4-CH.sub.3 
CH.sub.3 
cyclohexyl N H H 2931, 1700, 1507, 
1422, 1378, 1274, 
1178, 1003, 671 
94 4-C(CH.sub.3 ).sub.3 
CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H 2959, 1694, 1420, 
1364, 1271, 1230, 
1020, 656, 671 
95 4-C(CH.sub.3).sub.3 
CH.sub.3 
n-C.sub.4 H.sub.9 
N H H 2960, 1699, 1426, 
1379, 1274, 1210, 
1001, 671 
96 4-C(CH.sub.3).sub.3 
CH.sub.3 
n-C.sub.8 H.sub.17 
CH H H n.sub.D.sup.25 1.5158 
97 4-C(CH.sub.3).sub.3 
CH.sub.3 
n-C.sub.8 H.sub.17 
N H H n.sub.D.sup.22 1.5096 
98 4-C(CH.sub.3).sub.3 
CH.sub.3 
n-C.sub.5 H.sub.11 
CH H H n.sub.D.sup.23 1.5176 
99 4-C(CH.sub.3).sub.3 
CH.sub.3 
n-C.sub.5 H.sub.11 
N H H n.sub.D.sup.23 1.5135 
100 4-C(CH.sub.3).sub.3 
CH.sub.3 
--HC(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 
CH H H n.sub.D.sup.23 1.5268 
101 4-C(CH.sub.3).sub.3 
CH.sub.3 
--HC(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 
N H H n.sub.D.sup.23 1.5192 
102 4-C(CH.sub.3).sub.3 
CH.sub. 3 
iso-C.sub.4 H.sub.9 
CH H H n.sub.D.sup.22 1.5190 
103 4-C(CH.sub.3).sub.3 
CH.sub.3 
iso-C.sub.4 H.sub.9 
N H H 2960, 1694, 1419, 
1267, 1244, 1099, 
1018, 804 
104 4-C(CH.sub.3).sub.3 
CH.sub.3 
(CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 -- 
CH H H n.sub.D.sup.23 1.5215 
105 4-C(CH.sub.3).sub.3 
CH.sub.3 
--HC(CH.sub.3)C.sub.5 H.sub.11 --n 
CH H H 2960, 1694, 1408, 
1375, 1325, 1298, 
1099, 759 
106 4-C(CH.sub.3).sub.2 C.sub.2 H.sub.5 
CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H n.sub.D.sup.20 1.5242 
107 4-C(CH.sub.3).sub.2 C.sub.2 H.sub.5 
CH.sub.3 
n-C.sub.4 H.sub.9 
N H H n.sub.D.sup.22 1.5183 
108 4-C(CH.sub.3).sub.2 C.sub.2 H.sub.5 
CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H n.sub.D.sup.25 1.5194 
109 4-C(CH.sub.3).sub.2 C.sub.2 H.sub.5 
CH.sub.3 
n-C.sub.6 H.sub.13 
N H H n.sub.D.sup.25 1.5146 
110 4-C(CH.sub.3).sub.2 C.sub.3 H.sub.7 n 
CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H n.sub.D.sup.25 1.5221 
111 4-C(CH.sub.3).sub.2 C.sub.3 H.sub.7 n 
CH.sub.3 
n-C.sub.4 H.sub.9 
N H H n.sub.D.sup.25 1.5172 
112 4-C(CH.sub.3).sub.2 C.sub.3 H.sub.7 n 
CH.sub.3 
n-C.sub.4 H.sub.13 
CH H H n.sub.D.sup.23 1.5154 
113 4-C(CH.sub.3).sub.2 C.sub.3 H.sub.7 -i 
CH.sub.3 
n-C.sub.4 H.sub.9 
CH H H n.sub.D.sup.26 1.5176 
114 4-C(CH.sub.3).sub.2 C.sub.3 H.sub.7 -i 
CH.sub.3 
n-C.sub.4 H.sub.9 
N H H n.sub.D.sup.26 1.5187 
115 4-C(CH.sub.3).sub.2 C.sub.3 H.sub.7 -i 
CH.sub.3 
n-C.sub.6 H.sub.13 
CH H H n.sub.D.sup.22 
__________________________________________________________________________ 
1.5222 
The novel compounds have an excellent action on a broad spectrum of 
plant-pathogenic fungi, especially from the Ascomycetes and Basidiomycetes 
classes. Some of them have a systemic action and may be used as soil or 
foliar herbicides. They may also be used for protecting materials, inter 
alia for combatting wood-destroying fungi such as Coniophora puteana and 
Polystictus versicolor. The novel active ingredients also effectively 
combat molds and wood-discoloring fungi such as Pullularia pullulans. 
Further, the novel compounds are effective on Candida albicans and 
Trichophyton mentogrophytes. 
The fungicidal compounds are of particular interest for combatting a large 
number of fungi in various crops or their seed, especially wheat, rye, 
barley, oats, rice, Indian corn, cotton, soybeans, coffee, sugarcane, 
fruit, ornamentals in horticulture, and vegetables, such as cucumbers, 
beans and Cucurbitaceae. 
The novel compounds are particularly suitable for combatting the following 
diseases: Pseudocercosporella herpotrichoides in cereals, Erysiphe 
graminis in cereals, Erysiphe cichoriacearum in Cucurbitaceae, Podosphaera 
leucotricha in apples, Uncinula necator in grapes, Puccinia species in 
cereals, Rhizoctonia solani in cotton, Ustilago species in cereals and 
sugarcane, Venturia inaequalis (scab) in apples, Septoria nodorum in 
wheat, Botrytis cinerea in strawberries and grapes, and Rhynchosporium 
secalis and Pyrenophora teres in cereals. 
The active ingredients may simultaneously suppress the growth of two or 
more of the said fungi, and are excellently tolerated by plants. Some of 
the active ingredients also have curative properties, i.e., the agents may 
be applied after infection of the plants by the pathogen and success is 
still ensured. 
The fungicidal agents contain from 0.1 to 95, and preferably from 0.5 to 
90, wt% of active ingredient. The application rates depend on the type of 
effect desired, and range from 0.1 to 5 kg of active ingredient per 
hectare. 
The novel active ingredients may also be mixed and applied with other 
active ingredients, e.g., herbicides, insecticides, growth regulators, 
other fungicides and fertilizers. When mixed with other fungicides, the 
spectrum of fungicidal action is in many cases increased; with a number of 
these fungicidal compositions, synergistic effects also occur, i.e., the 
fungicidal action of the combination product is greater than the effect of 
the individual components added together. Examples of fungicides which can 
be combined with the novel compounds are as follows: 
sulfur 
dithiocarbamates and derivatives thereof, such as 
ferric dimethyldithiocarbamate 
zinc dimethyldithiocarbamate 
zinc ethylenebisthiocarbamate 
tetramethylthiuram disulfide 
manganese ethylene bis-dithiocarbamate 
manganese-zinc ethylenediamine-bisdithiocarbamate 
ammonia complex of zinc-(N,N'-ethylene)-bisdithiocarbamate and 
N,N'-polyethylene-bis-(thiocarbamoyl)-disulfide 
ammonia complex of zinc-(N,N'-propylene-bisdithiocarbamate) and 
N,N'-polypropylene-bis-(thiocarbamoyl)-disulfide 
nitro derivatives, such as 
dinitro-(1-methylheptyl)-phenylcrotonate 
2-sec-butyl-4,6-dinitrophenyl-3,5-dimethylacrylate 
2-sec-butyl-4,6-dinitrophenylisopropylcarbonate 
diisopropyl 5-nitroisophthalate 
heterocyclic structures, such as 
2-heptadecyl-2-imidazoline acetate 
2,4-dichloro-6-(o-chloroanilino)-s-triazine 
O,O-diethylphthalimidophosphorothionate 
5-amino-1-[bis-(dimethylamino)-phosphynyl]-3-phenyl-1,2,4-triazole 
2,3-dicyano-1,4-dithiaanthraquinone 
2-thio-1,3-dithio-(4,5-b)-quinoxaline 
methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate 
2-methoxycarbonylaminobenzimidazole 
2-[furyl-(2)]-benzimidazole 
2-[thiazolyl-(4)]-benzimidazole 
N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide 
N-trichloromethylthiotetrahydrophthalimide 
N-trichloromethylphthalamide 
N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide 
5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole 
2-thiocyanomethylthiobenzthiazole 
1,4-dichloro-2,5-dimethoxybenzole 
4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone 
pyridine-2-thio-1-oxide 
8-hydroxyquinoline and its copper salt 
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne-4,4-dioxide 
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne 
2-methyl-5,6-dihydro-4-H-pyran-3-carboxanilide 
2-methyl-furan-3-carboxanilide 
2,5-dimethyl-furan-3-carboxanilide 
2,4,5-trimethyl-furan-3-carboxanilide 
2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide 
N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide 
2-methyl-benzoic acid anilide 
2iodobenzoic anilide 
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-tridecyl-morpholine and its salts 
2,6-dimethyl-N-cyclododecyl-morpholine 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-yl-ethyl]-1-H-1,2,4-triazo 
le 
1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1-H-1,2,4-tri 
azole 
N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazol-ylurea 
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone 
1-(4-chlorophenoxy)-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-[2-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimide 
hexachlorobenzene 
D,L-methyl-N-(2,6-dimethylphenyl)-N-(2-furoyl)-alanate 
methyl D,L-N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)-alanate 
N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-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-isopropyl-carbamoylhydantoin 
N-(3,5-dichlorophenyl)-1,2-dimethyl-cyclopropane-1,2-dicarboximide 
2-cyano-N-(ethylaminocarbonyl)-2-(methoximino)-acetamide 
1-(2-(2,4-dichlorophenyl)-pentyl)-1H-1,2,4-triazole 
2,3-difluoro-alpha-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol. 
The novel active ingredients are applied for instance in the form of 
directly sprayable solutions, suspensions (including high-percentage 
aqueous, oily or other suspensions), dispersions, emulsions, oil 
dispersions, pastes, dusts, broadcasting agents, or granules by spraying, 
atomizing, dusting, broadcasting or watering. The forms of application 
depend entirely on the purpose for which the agents are being used, but 
they must ensure as fine a distribution of the novel active ingredients as 
possible. 
For the preparation of solutions, emulsions, pastes and oil dispersions to 
be used direct or after emulsification in water, mineral oil fractions of 
medium to high boiling point, such as kerosene or diesel oil, further 
coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic 
and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, 
tetrahydronaphthalene, alkylated naphthalenes and their derivatives such 
as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, 
cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly 
polar solvents such as dimethylformamide, dimethyl sulfoxide, and 
N-methylpyrrolidone, and water are suitable. 
Aqueous formulations may be prepared from emulsion concentrates, pastes, 
oil dispersions or wettable powders by adding water. To prepare emulsions, 
pastes and oil dispersions the ingredients as such or dissolved in an oil 
or solvent may be homogenized in water by means of wetting or dispersing 
agents, adherents or emulsifiers. Concentrates which are suitable for 
dilution with water may be prepared from active ingredient, wetting agent, 
adherent, emulsifying or dispersing agent and possibly solvent or oil. 
Examples of surfactants are: alkali metal, alkaline earth metal and 
ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, 
phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl 
sulfonates, alkali metal and alkaline earth metal salts of 
dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol 
sulfates, alkali metal and alkaline earth metal salts of fatty acids, 
salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of 
sulfated fatty alcohol glycol ethers, condensation products of sulfonated 
naphthalene and naphthalene derivatives with formaldehyde, condensation 
products of naphthalene or naphthalenesulfonic acids with phenol and 
formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated 
isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, 
alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl 
polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide 
condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, 
ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, 
sorbitol esters, lignin, sulfite waste liquors and methyl cellulose. 
Powders, dusts and broadcasting agents may be prepared by mixing or 
grinding the active ingredients with a solid carrier. 
Granules, e.g., coated, impregnated or homogeneous granules, may be 
prepared by bonding the active ingredients to solid carriers. Examples of 
solid carriers are mineral earths such as silicic acid, silica gels, 
silicates, talc, kaolin, attapulgus day, limestone, lime, chalk, bole, 
loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium 
sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium 
sulfates, ammonium phosphate, ammonium nitrate, and ureas, and vegetable 
products such as grain flours, bark meal, wood meal, and nutshell meal, 
cellulosic powders, etc. 
Examples of such formulations are given below. 
I. 90 parts by weight of compound 1 is mixed with 100 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 25 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 the compound obtainable in accordance with 
Example 39 is dissolved in a mixture consisting of 30 parts by weight of 
cyclohexanone, 30 parts by weight of isobutanol, and 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 44 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. 20 parts by weight of compound 80 is well mixed with 3 parts by weight 
of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts 
by weight of the sodium salt of a lignin-sulfonic acid obtained from a 
sulfite waste liquor, and 60 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. 5 parts by weight of the compound obtainable in accordance with Example 
40 is intimately mixed with 95 parts by weight of particulate kaolin. A 
dust is obtained containing 5% by weight of the active ingredient. 
VII. 30 parts by weight of compound 76 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 41 is intimately mixed with 30 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. 
IX. 20 parts of compound 46 is intimately mixed with 2 parts of the calcium 
salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol 
ether, 2 parts of the sodium salt of a phenolsulfonic 
acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral 
oil. A stable oily dispersion is obtained. 
The following experiments demonstrate the biological action of the novel 
compounds. The agents used for comparison purposes were the prior art 
active ingredients N-trichloromethylthiotetrahydrophthalimide (A) and 
N-trichloromethylthiophthalamide (B) particularly suitable for combatting 
Botrytis. 
EXPERIMENT 1 
Action on Botrytis cinerea in pimientos 
Pimiento seeldings of the "Neusiedler Ideal Elite" variety were sprayed, 
after 4 to 5 leaves were well developed, to runoff with aqueous 
suspensions contaning (dry basis) 80% of active ingredient and 20% of 
emulsifier. After the sprayed-on layer had dried, the plants were 
sprinkled with a conidial suspension of the fungus Botrytis cinerea, and 
placed at 22.degree. to 24.degree. C. in a chamber of high humidity. After 
5 days, the disease had spread to such a great extent on the untreated 
plants that the necroses covered the major portion of the leaves. 
The results of this experiment show that for instance compounds nos. 1, 25, 
39, 44 and 80, applied as 0.05% spray liquors, had a better fungicidal 
action (e.g., 90%) than prior art active ingredient A (e.g., 70%). 
EXPERIMENT 2 
Action on Plasmopara viticola 
Leaves of potted vines of the Muller-Thurgau variety were sprayed with 
aqueous suspensions containing (dry basis) 80% of active ingredient and 
20% of emulsifier. To assess the duration of action, the plants were set 
up, after the sprayed-on layer had dried, for 10 days in the greenhouse. 
Then the leaves were infected with a zoospore suspension of Plasmopara 
viticola. The plants were first placed for 16 hours in a water 
vapor-saturated chamber at 24.degree. C. and then in a greenhouse for 8 
days at from 20.degree. to 30.degree. C. To accelerate and intensify the 
sporangiophore discharge, the plants were then again placed in the moist 
chamber for 16 hours. The extent of fungus attack was then assessed on the 
undersides of the leaves. 
The results of the experiment show that for instance compounds nos. 40, 44 
and 76, applied as 0.05% spray liquors, had a better fungicidal action 
(e.g., 97%) than prior art active ingredient B (e.g., 90%). 
EXPERIMENT 3 
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 of this experiment show that for example compounds nos. 2, 40, 
41, 46, 58, 67, 68, 69 and 70, applied as 0.05% spray liquors, had a good 
fungicidal action (e.g., 97%).