DIURETHANES HERBICIDES, LEUR FABRICATION ET UTILISATION

HERBICIDALLY ACTIVE DIURETHANES AND THEIR MANUFACTURE AND USE

Abrégé anglais

ABSTRACT OF THE DISCLOSURE
Novel diurethanes of the general formula I
(I)
<IMG>
(wherein R1 represents C1-C4-alkyl or phenylethyl, R2 represents
C1- C4-alkyl, halogeno-C1-C4-alkyl, C2-C4-alkenyl or -alkynyl or
halogeno-C2-C4-alkenyl or -alkynyl, Y represents H or F and X
represents O or S) and their manufacture. The novel compounds
of the general formula I have a herbicidal action and accordingly
may be made up with suitable carriers into herbicidal preparations
and may be used for protecting living plants and crop areas against
weeds.

Revendications

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A diurethane of the general formula I
<IMG> (I)
in which R1 represents a C1-C4-alkyl or phenylethyl group, R2
represents a C1-C4-alkyl, halogeno-C1-C4-alkyl, C2-C4-alkenyl,
halogeno-C2-C4 alkenyl, C2-C4-alkynyl or halogeno-C2-C4-alkynyl
group, Y represents a hydrogen or fluorine atom and X represents
an oxygen or sulphur atom.
2. A compound as claimed in claim 1, wherein R1 repre-
sents a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-
butyl or 2-phenylethyl group and R2 represents a methyl, ethyl,
propyl, isopropyl, butyl, isobutyl, sec.-butyl, allyl, propargyl,
chlorethyl, l-chlormethylethyl, 4-chlorobutynyl, l-methylpropynyl
or 4-chlorobutenyl group.
3. N-Ethyl-3-fluorocarbanilic acid [3-(ethylthiocarbonyl-
amino)-phenyl] ester.
4. 3-Fluoro-N-methylcarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
5. N-Ethyl-3-fluorocarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
6. N-Ethyl-3-fluorocarbanilic acid (3-(methylthiocarbonyl-
aminophenyl)-phenyl] ester.
28

7. 4-Fluoro-N-methylcarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
8. 4-Fluoro-N-methylcarbanilic acid [3-(methylthiocar-
bonylamino)-phenyl] ester.
9. N-Ethyl-4-fluorocarbanilic acid [3-(methylthiocar-
bonylamino)-phenyl] ester.
10. N-Ethyl-4-fluorocarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
11. N-Ethyl-4-fluorocarbanilic acid (3-ethoxycarbonyl,
aminophenyl) ester.
12. N-Ethyl-3-fluorocarbanilic acid (3-ethoxycarbonyl-
aminophenyl) ester.
13. 3-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonyl-
aminophenyl) ester.
14. 3-Fluoro-N-methylcarbanilic acid [3-(methylthio-
carbonylamino)-phenyl] ester.
15. 3-Fluoro-N-methylcarbanilic acid [3-(ethylthiocar-
bonylamino)-phenyl] ester.
16. 4-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonyl-
aminophenyl) ester.
17. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxy-
carbonylaminophenyl) ester.
18. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxy-
carbonylaminophenyl) ester.
19. N-Ethyl-3-fluorocarbanilic acid [3-(1-methylethoxy-
29

carbonylamino)-phenyl ester.
20, N-Ethyl-4-fluorocarbanilic acid [3-(l-methylethoxy-
carbonylamino)-phenyl] ester.
21. 4-Fluoro-N-methylcarbanilic acid [3-(1-methylethoxy-
carbonylamino)-phenyl] ester.
22. N-Ethyl-4-fluorocarbanilic acid [3-(ethylthiocar-
bonylamino)-phenyl] ester.
23. 4-Fluoro-N-methylcarbanilic acid [3-(ethylthiocar-
bonylamino)-phenyl] ester.
24. 3-Fluoro-N-methylcarbanilic acid [3-(2-propynyloxy-
carbonylamino)-phenyl] ester.
25. N-Ethyl-3-fluorocarbanilic acid [3-(2-propynyloxy-
carbonylamino)-phenyl] ester.
26. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-
(ethylthiocarbonylamino)-phenyl] ester.
27. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-
(l-methylethoxycarbonylamino)-phenyl] ester.
28. N-Ethyl-4-fluorocarbanilic acid (3-allyloxycarbonyl-
aminophenyl) ester.
29. N-Ethyl-4-fluorocarbanilic acid [3-(2-propynyloxy-
carbonylamino)-phenyl] ester.
30. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyl-
oxycarbonylaminophenyl) ester.
31. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-me-
thoxycarbonylaminophenyl) ester.

32. N-Ethyl-2-fluorocarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
33. N-Ethyl-3,4-difluorocarbanilic acid (3-methoxycar-
bonylaminophenyl) ester.
34. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-
ethoxycarbonylaminophenyl) ester.
35. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-
(ethylthiocarbonylamino)-phenyl] ester.
36. 3-Fluoro-N-methylcarbanilic acid [3-(1-methylethoxy-
carbonylamino)-phenyl] ester.
37. 3-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonyl-
aminophenyl) ester.
38. 3-Fluoro-N-ethylcarbanilic acid (3-allyloxycarbonyl-
aminophenyl) ester.
39. 4-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonyl
aminophenyl) ester.
40. N-Ethyl-3-fluorocarbanilic acid [3-(1-chloromethyl-
ethoxycarbonylamino)-phenyl] ester.
41. N-Ethyl-3,4-difluorocarbanilic acid (3-ethoxycarbonyl-
aminophenyl) ester.
42. N-Ethyl-3,4-difluorocarbanilic acid [3-(methylthio-
carbonylamino)-phenyl] ester.
43 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-
methoxycarbonylaminophenyl) ester.
44. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-
31

ethoxycarbonylaminophenyl) ester,
45, 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-
(methylthiocarbonylamino)-phenyl] ester.
46. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-
(ethylthiocarbonylamino)-phenyl] ester.
47. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(1-
methylethoxycarbonylamino)-phenyl] ester.
48. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(2-
propynyloxycarbonylamino)-phenyl] ester.
49. 3-Fluoro-N-propylcarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
50. 3-Fluoro-N-propylcarbanilic acid [3-(methylthiocar-
bonylamino)-phenyl] ester.
51. 3-Fluoro-N-propylcarbanilic acid (3-(ethoxycarbonyl-
aminophenyl)ester
52. N-Ethyl-3-fluorocarbanilic acid [3-(1-methyl-2-
propenyloxycarbonylamino)-phenyl] ester.
53. N-Ethyl-2-fluorocarbanilic acid [3-(1-methyl-2-
propenyloxycarbonylamino)-phenyl] ester.
54. N-Ethyl-4-fluorocarbanilic acid [3-(1-methyl-2-
propenyloxycarbonylamino)-phenyl] ester.
55. N-Butyl-3-fluorocarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
56. 3-Fluoro-N-methylcarbanilic acid [3-(2-methylpropoxy-
carbonylamino)-phenyl] ester.
32

57. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(1-
methyl-2-propenyloxycarbonylamino)-phenyl] ester.
58. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(1-
methyl- 2-propenyloxycarbonylamino)-phenyl] ester.
59. 3-Fluoro-N-methylcarbanilic acid [3-(1-methyl-2-
propenyloxycarbonylamino)-phenyl] ester.
60. 4-Fluoro-N-methylcarbanilic acid [3-(1-methyl-2-
propenyloxycarbonylamino)-phenyl] ester.
61. N-Butyl-4-fluorocarbanilic acid [3-(1-methyl-2-
propenyloxycarbonylamino)-phenyl] ester.
62. 4-Fluoro-N-methylcarbanilic acid [3-(2-methyl-
propoxycarbonylamino)-phenyl] ester.
63. 4-Fluoro-N propylcarbanilic acid [3-(1-methyl-2-
propenyloxycarbonylamino)-phenyl] ester.
64. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(2-
methylpropoxycarbonylamino)-phenyl] ester.
65. 4-Fluoro-N-propylcarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
66. 4-Fluoro-N-propylcarbanilic acid (3-ethoxycarbonyl-
aminophenyl) ester.
67. N-Butyl-4-fluorocarbanilic acid (3-methoxycarbonyl-
aminophenyl) ester.
68. N-Butyl-4-fluorocarbanilic acid (3-ethoxycarbonyl-
aminophenyl) ester.
69. 4-Fluoro-N-butylcarbanilic acid [3-(1-methylethoxy-
33

carbonylamino)-phenyl] ester.
70. 4-Fluoro-N-butylcarbanilic acid [3-(ethylthiocar-
bonylamino)-phenyl] ester.
71 N-Butyl-4-fluorocarbanilic acid [3-(2-propynyloxy-
carbonylamino)-phenyl] ester.
72. 4-Fluoro-N-propylcarbanilic acid [3-ethylthiocar-
bonylamino)-phenyl] ester.
73. 4-Fluoro-N-propylcarbanilic acid [3-(2-propynyloxy-
carbonylamino)-phenyl] ester.
74. N-Butyl-4-fluorocarbanilic acid [3-(methylthiocar-
bonylamino)-phenyl] ester.
75. N-Ethyl-2-fluorocarbanilic acid (3-ethoxycarbonyl-
aminophenyl) ester.
76. N-Ethyl-2-fluorocarbanilic acid [3-(methylthiocar-
bonylamino)-phenyl] ester.
77. N-Ethyl-2-fluorocarbanilic acid [3-ethylthiocar-
bonylamino)-phenyl] ester.
78. N-Ethyl-2-fluorocarbanilic acid [3-(1-methylethoxy-
carbonylamino)-phenyl] ester.
79. N-Ethyl-2-fluorocarbanilic acid [3-2-propynyloxy-
carbonylamino)-phenyl] ester.
80. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyl-
oxycarbonylaminophenyl) ester.
81. A process for the manufacture of a compound of the
34

general formula I given in Claim 1, in which R1, R2, Y and X have
the meanings given in claim 1, wherein (a) a compound of the gen-
eral formula
<IMG> ,
in which R2 and X have the meanings given above, is reacted in
the presence of an acid acceptor with an amine of the general
formula
<IMG> ,
in which R1 and Y have the meanings given above, or (b) a com-
pound of the general formula
<IMG> ,
in which R2 and X have the meanings given above, is reacted in
the presence of a tertiary organic base or is reacted in the form
of an alkali salt thereof with a carbamoyl chloride of the general
formula
<IMG> ,
in which R1 and Y have the meanings given above, each reaction being

carried out at a temperature within the range of from 0 to 100°C,
or (c) a nitro compound of the general formula
<IMG> ,
in which R1 and Y have the meanings given above, is catalytically
hydrogenated to form the corresponding amino compound which is
then reacted in the presence of an acid acceptor with a compound
of the general formula
Cl-CO-X-R2,
in which R2 and X have the meanings given above.
82. A method of protecting a living plant against weeds,
wherein the area in the vicinity of the living plant is treated
with a compound claimed in claim 1.
83. A method of protecting a living plant against weeds,
wherein the area in the vicinity of the living plant is treated
with a compound claimed in claim 2, 3 or 4.
84. A method of protecting a living plant against weeds,
wherein the area in the vicinity of the living plant is treated
with a compound claimed in claim 5, 6 or 7.
85. A method of protecting a living plant against weeds,
wherein the area in the vicinity of the living plant is treated
with a compound claimed in claim 8, 9 or 10.
86. A method of protecting a living plant against weeds,
36

wherein the area in the vicinity of the living plant is treated
with a compound claimed in claim 11, 12 or 13.
87. A method of protecting a living plant against weeds,
wherein the area in the vicinity of the living plant is treated
with a compound claimed in claim 14, 15 or 16.
88. A method of protecting a living plant against
37

weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 17, 18 or 19.
89. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 20, 21 or 22.
90. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 23, 24 or 25.
91. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 26, 27 or 28.
92. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 29, 30 or 31.
93. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 32, 33 or 34.
94. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 35, 36 or 37.
95. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 38, 39 or 40.
96. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 41, 42 or 43.
97. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 44, 45 or 46.
98. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 47, 48 or 49.
38

99. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 50, 51 or 52.
100. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 53, 54 or 55.
101. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 56, 57 or 58.
102. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 59, 60 or 61.
103. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 62, 63 or 64.
104. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 65, 66 or 67.
105. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 68, 69 or 70.
106. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 71, 72 or 73.
107. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 74, 75 or 76.
108. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
treated with a compound claimed in claim 77, 78 or 79.
109. A method of protecting a living plant against
weeds, wherein the area in the vicinity of the living plant is
39

treated with a compound claimed in claim 80.
110. A method as claimed in claim 82 wherein a single
compound of the general formula I is used for the treatment in an
amount within the range of from 1 to 5 kg per hectare.
111. A method as claimed in claim 82 wherein two or
more compounds of the general formula I are used for the treat-
ment in a total amount within the range of from 1 to 5 kg per
hectare.
112. A method of protecting a crop area against weeds,
wherein the crop area is treated with a compound of the general
formula I given in claim 1, in which R1, R2, Y and X have the
meanings given in claim 1.
113. A method as claimed in claim 112 wherein a single
compound of the general formula I is used for the treatment in
an amount within the range of from 1 to 5 kg per hectare.
114. A method as claimed in claim 112 wherein two or
more compounds of the general formula I are used for the treat-
ment in a total amount within the range of from 1 to 5 kg per
hectare.
115. A method as claimed in claim 112 wherein the crop
is a cotton crop.

Description

l~Z8~61
The present invention is concerned with new diurethanes,
with processes ~or theimanufactu~e c~ these compounds and with
thier use as herbicidal ,a,gents,
The herbicidal action of diurethanes is already known.
Known active substances of this kind have a selective herbicidal
action especially in beet crops (German Patent Specification No.
1,567,151) or in soya beans (German Patent Specification No.
2,638,897).
The problem upon which the present invention is based
has been to develop a herbicidal agent which has a very good ac-
tion against weeds that are difficult to control and, at the same
time, exhibits a tolerance especially in cotton crops.
This problem is solved according to the present invention
by the compounds of the general formula I, as defined below.
The present invention accordingly provides compounds
of the general formula I
;
2 -

61
- 3 -
O-CO~ ~ Y
. F ~I)
~ ~ X ~2
in which
R represents a Cl-C4-alkyl or ~henylethyl group, -~
R2 representq a al-C4-alkyl, halogeno-Cl-C4-alk~yl9
C2-C4-alke~yl, halogeno-C2-C4-alkenyl, C2-C4-
alkynyl or halogeno-C2-C4-alkynyl group,
Y represents a hydrogen or ~luorine atom an~
repre~ents an oxygen or sulphur atom.
~ he compounds of the present i.nvention, surpri-
~ingly, exhibit an outstanding tolerance in cotton crops
which i3 not the case with known compounds ol analogous
con~titution.
In addition, they have a very good action against
weeds that are di~iicult to control, ~or example
~maranthu~, Stellaria, Matricaria and others, which can
be controlled by both the pre-emergence and the post-
emergence methodsO
Application quantities within the range o~ ~rom 1
to a maximum o~ 5 kg of active subqtance per hectare are
generally su~ficient to control these seed weed~q, the
. ~ .
- , -

1~%~
compounds o~ the present invention exhibiting a selective
action aleo in useful plant crops other than cotton, for
example soya, ground-nut, potatoes, maize, rice, sorghum
and cerealsO When two or more compounds of the present
i~vention are used, the range o~ 1 to 5 kg refers of course
to the total application quar,tities o~ these compounds.
The present inve~tion accordingly also provides a
herbicidal preparation which comprises a compound o~ the
ge~eral formula I, in admixture or conjunction with a
suitable carrier. The preparation may of course contain
one or more compounds o~ the general ~ormula Io
The present invention further provides a method o~
protecting a living plant against weeds? wherein the
area in the vicinity of the living plant is treated with
a compourd of the general formula I.
~ he present invention further provides a method of
protecting a crop area against weeds, wherein the crop
area is treated with a compound of the general formula I.
~ he present invention further provides a pack which
compri~es a compound of the ~eneral formula I together
~ith instructions for it~ u~e as a herbicide.
~ he compounds of the present invention may be used
either ~in6~1y or in the form of mixtures with one another
or with other active substancesO If desired, other
plant-protecting agents and/or pesticides may be added,
dependin~ on the desired aimO

1128~!61
I~ a broadening o~ the range of action i~ intended,
other herbicides may also be added. As suitable herbici-
dally active co-components there may be mentioned, ~or
example, active ~ub~tances ~rom the groups of triazines,
aminotriazoles, anilides, diazines, uracils, aliphatic
carbo~ylic acid~ and halocarboxylic acids, substituted
benzoic acids and aryloxycarboxylic acids, hydrazides,
~mides, nitriles, esters o~ such carboxylic acids,
carbamic acid esters and thiocarbamic acid esters, ureas,
2,3,6-trichiorobenzylo~yisopropanol and thiocyanogen-
containing agents.
Furthermore, other additives may also be used, for
example non-phytotoxic additives which with herbiclde~
produce a synergistic increase in action, ~or example
wetting agents, emulsifi.ers, solYents and oily additi~res.
. The active compounds of the present invention or
mixtures contalning them are advan-tageously used in the
form of herbicidal preparations, for example powders,
strewable preparations, granule~ solution~, emuls.ions
or suspen~ions, with the addition of liquid ~nd~or solid
vehicle~ or diluents and, i~ desired, of surface-acti~e
agents, for example wetting, adhesive, emulsifying and/or
disper~ing auxiliary agent~.
Suitable liquid carrier~ are, for example, water,
aliphatic hydrocarbons, aromatic hydrocarbons, for example
benzene, toluene and xylene, cyclohexanone, isophorone,
dimethyl sulphoxide and dimethyl~ormamide, and also

~2~Q61
-- 6 --
mineral oil fractions.
~ uitable solid carriers are, for example, mineral
earth~, for example tonsil, silica gel, talcum9 kaolin,
attaclay, limestone and ~ilicic acid, and vegetable
products, for example meals.
As surface-active agents there may be mentioned,
for exa~ple, calcium li~nin sulphonate~ polyoxyethylene-
alkylphenol ethers, naphthalene~ulpho~ic acid~ and salts
thereo~, phenolsulphonic acid~ and salt~ thereof, for-
maldehyde condensatess fatty alcohol sulphates and also
sub~tituted benzene~ulphonic acids and salts thereof.
The proportion of the active ~ubstance or sub~tances
in the various herbicidal preparations may vary within
wide limits. ~or example 9 the preparations may contai~
approximately 5 to 95% by weight OL active substanca(~),
approximately 95 to 5~0 by weight of liquid or solid
carrler and al~o, if desired, up to 20~o by weight of
surface-active a~ent(s).
~ he active compounds may be applied in the usual
manner, ~or example with water a~ the oarrier in spray
liquor quantities o~ approximately 50 to 1000 litres/
hectare. It is al~o po~sible to apply the active com-
pounds by the so-called low-volume and ultra-low-volume
methods as well as to apply them in the form of ~o-called
microgranules.

llZ~361
-- 7 ~
~ s group~ repre~ented by the ~ymbol Rl in the
general ~ormula X there may be mentioned, for example,
methyl, ethyl, propyl, i60propyl, butyl, isobutyl, ~ec.-
butyl and 2-phenylethyl group~, and a~ groups represented
by the ~ymbol R2, ~or e~ample, methyl, ethyl, propyl,
i60propyl, butyl, isobutyl, sec.-butyl, allyl, propargyl,
chlorethyl, l-chloromethylethyl, 4-chlorobutynyl, 1-
methylpropynyl and 4-chlorobutenyl ~roup~. -
Compounds o~ the present invention which aredistin~uished by an out~tanding selective herbicidal
action are especially N-ethyl-3-Iluorocarbanilic acid
(3-etho~ycarbonylaminophenyl) ester, N-ethyl-3-~luoro-
carbanilic acid (3-metho~ycarbonylaminophenyl) ester, N-
ethyl-3-~luorocarbanilic acid C3-(1-methyleth~oxycarbony~-
ami.lo)-phenyl] e~ter, N-ethyl-4-fluorocarbanilic acid (3-
ethoxycarborlylaminophenyl) ester, 4-fluoro-N-methylcar-
banilic acid (3-ethoxycarbonvlaminophenyl) ester, N-
ethyl-3-fluorocarbanilic acid ~3-(1-methylethoxycarbonyl-
amino)-phenylJ est~r, ~-othyl-4-fluorocarbanilic acid
~ methylethoxycarbonylamino)-phen~rl] ester, 4-fluoro-
N-methylcarbanilic acid ~3~ methylethoxycarbonyl~nino)-
phenyl] ester, 3-~luoro-I~-methylcarbanilic acid [3-(1-
methylethoxycarbonylamino)-phenyl] e6ter, N-ethy1-3,4-
difluorocarbanilic acid (3-ethoxycarbonylaminophenyl)
e~ter and N-ethyl-2-~luorocarbanilic acid ~3-methoxycar-
bonylaminophenyl) ester.

~L28~i6~1L
The new compo~lds of the general formula I may
be manufactured, for example, by the process o~ the
- present invention, as dePined below.
The present invention accordingly further provides
a process for the manufacture of the compounds of the
general formula I, wherein
a) a compound of the general formula
O-CO-~l
~ ~-CO-~-~2
in which R2 and X have the meanings given abo~e, is
reacted with an amine of the general formula
Y
F
in which Rl and Y have the meanings given abo~e, in the
pre~ence o~ an aci.d acceptor, ~or examp].e with the
addition of an excess of the amine or of an inorganic
base, for e~ample a sodium hydroxide solution, sodium
carbonate or potassium carbonate, or a tertiary organic
base, for e~ample triethylamine, or
b) a compound of the general formula

1~28~61
CO-~-R2
in which R2 and X have the meanings ~iven above, is
reacted in the presence o~ a tertiary organic base, for
example triethylamine or pyridine, or is reacted in the
~o~m of an alkali salt thereof with a carbamoyl c~iloride
o~ the general formula
~ N-aO-Cl,
~?
in whlch ~ and Y have ~he meaning~ given above, each
reaation being carried out at a temperature withil the
range of from 0 to 100C, or
c) a nitro compound o~ the general ~ormula

l~Z8~6~
-- 10 --
o_ao~
~ ~ F
1~ N02
i21 which ~ and Y have the meanings given above, is
catalytically hydrogenated, ~or example by using nickel
in methanol, to fo~m the corresponding amino compound
which is then reacted with a compound of the general
formula
Cl-CO-~-R2
in ~hich R2 ~nd X have the meanings given above, in the
presence of an acid acceptor, *or example an inorganic
base, ~or example a ~odium hydroxide solution, ~odium
carbo~ate or potassium carbonate, or a tertiary organic
ba_e~ ~or e~ample trie~hy~ ine.
The compounds of the ~eneral formula I formed by
any one of t~e variants (a) to (c) may be isolated in ~he
usual man~er.
~ he compou~ds o~ the present i~lvention are soluble
in acetone, cyclohexanone, i~ophorone, tetrahydrofuran,
dimethylformamide, dimethyl sulphoxide and ethyl acetate.

~3.28~
~ he ~ollowing E~ample~ illu~trate the inventionO
Example 1 illustrates the manu~acture of the compounds of
the present lnvention and Examples 2 to 4 illustrate the
po~ible way~ o~ using the compounds o~ the present
invention and, in the case of Example 4, compares their
herbicidal action with that o~ k~o~m compounds.
~5~ ~
N-~thyl-3-fluorocarbanilic acid t3-(ethylthiocarbon~l-
amino)-phenyl] ester
~ o a solution oP 13~9 g (0.1 mole) of N-ethyl-3-
fluoroaniline in 70 ml of ethyl acetate there were added
dropwi~e, while stirring and cooling to 10 to 15C, a
~olution o~ 26.0 g (0.1 mole) of chlorofor~ic acid C3-
(ethylthiocarbcnylamino)-phenyl] ester in 70 ml o~ ethyl
acetate and, at the same time, a solution o* 13.8 g (0.1
mole) of potassium carbor.ate in 50 ml of w~ter~ ~tirr~ng
wa~ continued for 30 minutes at 15C, and the organic
phase was thon separated and, with the addition of ice,
washed with dilute hydroc~ilorio acid ~ld water. After
drying with magnesium sulphate, the mixture wa8 concen-
trated by evaporation under reduced pressure. The
residue after evaporation was recrystallized from ethyl
acetate/pentane.
Yield: 29~4 g - 81~ o~ the theoretical yield of ~-ethyl-
~3-fluorocarbanilic acid ~-(ethylthio-
carbonylami~o)-phenyl] ester.

l~Z8~6
-- 12 --
M.p.: 127~.
~ he ~ollowing compounds of the present invention may
be manu~actured in an analogous manner.
Name of the compound Physical Constant
. .
3-~luoro-N-methylcarbanilic acid
(3-methoxycarbonylaminophenyl) ester M~p.: 105-107C
N-Eth~1-3-~luorocarbanilic acid (3- O
methoxycarbonylaminophelly].) ester Mopo 108-109 C
~thyl-3-fluorocarbanilic acid [3-
(methylthiocarbonyla~i~o)-phenyl~ O
ester Mop~ 125-127 a
~-Fluoro-N~methylcarbanilic acid
(3-methoxycarbonylaminophenyl) e~ter M.p.: 96-97C
4-~luoro-N-methylcarbanilic acid
[3-(methylthiocarbonylamino)-
phenyl] ester M.p.: 106-108C
N-Ethyl-4-~luorocarbanilic acid
~3-(methylthioca~bo~yla~ino)-
phenyl] ester M.p.: 143-144C
N-Ethyl-4 ~luorocarbanilic acid
(3-~ethoxycarbonyl~inophenyl)
est~r M.p.: 117-118C
N-~thyl-4-~luorocarbanilic acid
(3-ethoxycarbonylamillophenyl) ester M.p.: 76-7'la
thyl-3-~luorocarbanilic acid
(3-ethoxycarbonylaminophenyl) est~r M~po 122C
3-~luoro-N-methylcarbanilic acid
(3-ethoxycarbonylaminophenyl) ester Mopo 91-92C
~-~luoro-N-methylcarbanilic acid
[3-(methylthiocarbonylamino)-
phenyl~ ester ~I~po 116C
~-~luoro-N-methylcarbanilic acid
~3-(ethylthiocarbonylamino)-
phenyl] ester M.p.: 124-125C

1~28~61
- 13 -
.
Name of the compound Phy~ical Constant
4-~luoro~N-methylcarbanilic acid (3~ 20
ethoxycarbonylaminophenyl) ester nD : 1.5472
4-~luoro-~-(2-phe~ylethyl)-carbanilic
acid (3-methoxycarbonyl~ninophenyl) 0
ester M.p.: 137 C
4-Fluoro-N (2-phenylethyl)-carbanilic
acid (3~ethoxycarbonylaminophenyl) O
es-ter M~p.: 103-104 C
N-~thyl-3-fluorocarbanilic acid t3-
(1 ~ethylethoxycarbonylamino)-
phenyl] ester M~po 98C
h~-Ethyl-4-fluorocarbanilic acid C~-(l-
methylethoxycarbo~yl~nino) phenylJ
ester M~po 84-86C .
4-~luoro-~-methylcarbanilic acid C3-
(l~methylethoxycarbonyla~ino)- O
phenyl] ester M.p.: 88 C
N-~thyl-4-fluorocarbanilic acid ~3-
(ethylthiocarbonyl~nino)-phenyl] 0
ester Mop~ 79 C
4-~luoro-N-methylcarbanilic-acid [3-
(ethylthiooarbonylamino)-phenyl]
e~ter Mopo 97-99C
3-Fluoro-N-metllylcarbanilic acid ~3~
t2-propynyloxycarbonylamino)-phenyl]
ester M.p~: 142-144C
N-Ethyl 3-~luorocarbanilic acid ~3-
(2-propynyloxycarbonyl~nino)-phenyl]
ester M~po 148-150C
4-Fluoro-N-(2-phenylethyl)-carbanilic
acid C3-tethylthiocarbonylamino)-
phengl] ester Mop~ 117C
4-~luoro-N-(2-phenylethyl)-carbanilic
acid [3-(1-methylethoxycarbonylamino~-
phenylJ ester M.p.: 81-83C
N-Ethyl-4-fluorocarbanilic acid (3- 0
allyloxycarbonylaminophenyl) ester Mop~ 73-74 C

llZ~3~6~
Name of the compound Physical Constant
,
N-Ethyl-4-~luorocarbanilic acid ~3-
(2-propynyloxycarbonylamino)-phenyl]
ester M.p.: 7g-80C
4-Fluoro-N-(2-phenylethyl)-carbanilic
acid (3-allyloxycarbonylami~ophenyl) O
ester ~ M~p.: 81 C
~-~luoro-~-(2-phenylethyl)-carbanilic
acid (3-methoxycarbonylaminophenyl) 0
e~ter Mop~ 112-113 C
~-~thyl-2-fluorocarbænilic acid (3-
methoxycarbonylaminophenyl) ester M.p.: 106-107C
N-Ethyl-3,4-difluorocarbanilic acid
(3-methoxycarbonylaminophenyl) ester M.p.: 121-122C
3-~luoro-N-(2-phenylethyl)-carbanilic
acid (3-etho~ycarbonylaminophenyl) O
ester M.p.: 115 C
3-~luoro-N-(2-phenylethyl)-carbanilic
acid [3-(ethylthiocarbonylamino)- O
phenyl~ ester , M~po ~1-93 C
3-~luoro-~-methylcarbanilic acid [3-
(l-methylethoxycarbonylamino)-
phenyl] e~ter M.p~: 74-76C
3-~luoro-N-methylcarbanilic acid (3-
allyloxycarbonylaminophenyl) cster Mop~ 78-80C
3-~luoro-N-e~îylcarbanilic acid (3-
allylo~ycarbonylaminophenyl) ester Mop~ 101-10~C
4-Fluoro-~-methylcarbanilic acid (3- 20
allyloxycarbonylaminophenyl) ester nD : lo 5536
N-Ethyl-3-fluorocarbanilic acid ~3-(1-
chloromethylethoxyc~rbonylamino)-
phenyl] e~ter M~po 68-70C
N-Ethy1-3,4-di~luorocarbanilic acid
(3-ethoxycarbonylaminophenyl) e~ter M.p.: 69-70C
N-~thyl-3,4-di~luorocarbanilic acid
[3-(methylthiocarbonylamino)-phenyl] O
ester M~po 130-132 C

1~28~!6~
- 15 -
Name o~ the eompound Phy~ical Con~tant
2-~luoro-~-(2-phenylethyl)-carbanilie
aeid (3-methoxycarbonylaminophenyl)
e~ter M~p.: 125-126C
2-~luoro-N-(2-phe~ylethyl)-carbanilie
aeid (3-ethoxycarbonylaminophenyl)
ester M.p.: 128-130C
2-Fluoro-N-(2-phenylethyl)-carbanilie
aeid [~-(methylthiocarbonylamino)- .
phenyl~ e~ter M.p.: 148-149C
2-~luoro-N-(2-phenylethyl)-earbanilie
acid l3-(ethylthiocarbonylamino)-
phenyl] ester M~po 124C
2-Fluoro-N-(2-phenylethyl)-earbanilic
aeid ~3~ methylethoxyearbonylamino)-
phenyl] e~ter M.p.: 109-110C
3-~luoro-N-propylearbanilie aeîd (3-
methoxyearbonyla~inophenyl) ester M.p.: 90-92C
3-Fluoro N-propvlcarbanilic aeid [3-
(methylthioc~rbonylamino)-phenyl]
ester Mop~; 10~-lQ5C
3-Fluoro-N-propylearbanilie aeid (3-
et.hoxyearbonylaminophenyl) e.C~ter M~p~. 1 n3_10sa
N-~thyl-3-~luorocarbanil~o aeid [3-
(l-methyl-2-proponyloxyearbonylamino)-
~henyl] est.er M.p.: 100-101C
N-Ethyl-2-~luo~oc~rbanilie acid ~3-
(l-methyl-2-propenyloxycarbollylamino)-
phen~rl~ e~ter Mop~ los-lloa
N-Ethyl-4-fluorocarbanilie aeid ~3-(1-
methyl-2-propenylo~yearbonylamino)-
phenyl] e~ter M.p.: 73-74C
N-Butyl-3-~luoroearbanilie aeid (3-
me~hoxye~rbonylaminophenyl) ester M.p.: 79-80C
3-~luoro-~-methylearbanilie aeid [3-
(2-methylpropoxyearbonylamino)-
phenyl] e~ter M.p.: 94-95C

~128
6 ~
Name of the compound Phy6ical constant
4-Eluoro-~-(2-phenylethyl)-carballilic
acid ~3~ methyl-2-propenylo~y- 20
carbonylamino~-phenyl~ ester nD : 1.5578
3-Fluoro-N-(2-phenylethyl)-carbanilic
acid ~3-(1-methyl-2-propenyloxy- 20
carbonylamino)-phenyl] ester nD : 1.5632
3-Fluoro-N-methylcarbanilic acid ~3-
(l-methyl-2-propenylo~ycarbonylamino)- 20
phenyl] ester nD : 1.5509
4-Fluoro-l~-methylcarbanilic acid ~3-
methyl-2-propenyloxycarbonylamino)- 20
phenyl] ester nD : 1.5465
N-~ut~1-4-~luorocarbanilic acid C3-
(l-methyl-2-propenylo~ycarbonylamino)- 20
phenyl] ester nD : lo 5298
4-~luoro-N-methylcarbanilic acid ~3-
(2-methylpropoxycarbonylamino)- 20
phen~l] ester nD : 1.531~ ~
4-Eluoro-~-propylcarbanilic acid [3- t
(l-metnyl-2-propenyloxycarbonyl~nino)-
phenyl] ester Mop~ 75-76C
N-Ethyl-2-~l~orocarbanilic acid (3-
ethoxycarbonylaminophenyl) ester M.p.: 151-153C
N-Ethyl-2-fluorocarb~nilic acid [3-
(methylthiocarbonylamino)-phenyl~
ester M~p~o 150-162C
N-Eth~ 2-~luoroca~b~lilic acid [3-
(ethylthiocarbonylamino)-ph~nyl]
ester M.p.: 146-147C
N~Ethyl~2-~luorocarbanili~ acid ~3-
(l-methylethoxyoarbo~ylamino)-phenyl]
e~ter M.p.: 126-127C
N-~thyl-2-~luorocarb~lilic ac~d [3-
(2-propynyloxycarbon~rlamino)-phenyl]
ester M.p.: 150C

2 8
- 17 -
Name of the compound Physical Con~tant
2-~luoro-N-(2-phen~lethyl)-carbanilic
acid (~-allyloxycarbonylaminophenyl)
e~ter M~p.: 72-73a
2-~luoro-~(2-phenylethyl)-carbanilic
acid [~-(2-methylpropoxycarbonylamino)-
phenyl] ester M.p.: 57-58C
4-Fluoro-N-propylcarbanilic acid (3-
methoxycarbonylaminophenyl) e~ter nD : 1.5345
4-~luoro-I~-propylcarbanilic acid (3-
etho~ycarbonylaminophenyl) ester Mop~ 64-66C
N-~utyl-4-fluorocarbani.lic acid (3-
metho~ycarbonylaminophenyl) ester nD : lo 5322
N-~utyl-4-fluorocarbanilic acid (3- 20
etho~ycarbonylaminophenyl) ester nD : 1.5305
4-~luoro-N-butylcarbanilic acid [3-
(l-methylethoxycarljonylamino)- O '
phenyl] e~ter ~I.p.: 81-83 C
4-~luoro-N-butylcarbanilic acid [3-
(ethyithiocarbonyl~mino)-phenylJ O
e~ter Mop~ 73-75 C
N-~utyl-4-~luorocarbanilic acid 3-
(2-propynyloxycarbonylamino)-phenylJ ~0
e~ter nD : 105439
4-Fluoro-I~propylcarbanilic acid ~3-
(ethylthiocarbonylamino)-phenyl]
ester ;~.p.: 53-55C
4-~luoro-N-propylcarbanili.c acid [3-
(2-propynyloxycarbonylamino)-phenyl] 20
eeter nD : 105461
N-~utyl-4-~luorocarbanilic acid C3-
(methylthlocarbonylamino)-phenyl] 0
ester M~p.: 85-89 C
2-Fluoro-N-(2-phenylethyl)-carbanili.c
acid C3-~2-propynyloxycarbonylamino)-
phenyl] e~ter Mop~ 93-94C

1~21
-- 18 --
In a series o~ te3ts carried out in a greenhouse,
the compounds o~ the pre~ent invention listed in the
Table below were each sprayed in accordance with the post-
emergence method at a rate o~ application o~ 5 kg o*
active substance per hectare, emulsi~ied in 500 litres
o~ water per hectare, on to Brassica and Solanum as the
test plants. 3 week~ a~ter the treatment the results
thereo~ were evaluated and expressed by a numerical
~cale extending from O to 4, the value O representing no
action and the value 4 representing destrvction of the
plant.
A~ will be seen frorn the Table, destruction of the
plant~ wa~ achieved.
Cornpound of_ he inventlon Solanum Brassica
3-Fluoro-N-methylcarbanilic acid (3-
methoxycarbonylaminophenyl) ester 4 4
N-Ethyl-3-~luorocarbanilic acid (3-
methoxycarbonylaminophen~l) ester 4 4
N-Ethyl-3-~luorocarbanilic acid C3-
(methylthiocarbonylamino)~phellyl~
ester 4 4
4-~luoro-N-methylcarbanllic acid (3-
metho~ycarbonylaminophenyl) ester 4 4
4-~luoro-N-methylcarbanilic acid ~3-
(methylthiocarbonylamino)-phenyl]
e~ter 4 4
N-Ethyl-4-*luorocarbanilic acid ~3-
(methylthiocarbonylamino)-phenylJ
e~ter 4 4

~Z~3~6~ :
!
- 19 ~- j
~ompound o~ the invention Solanum Bra~sica 1.
N-Ethyl-4-fluorocarbanilie acid (3-
metho~ycarbonylaminophenyl) e~ter 4 4
N-~thyl-4-fluoroearb~nilie acid (3-
ethoxyearbonylaminophenyl) ester 4
N-~thyl-3-~luoroearbanilie aeid (3- -
etho~yearbonylaminophenyl) e~ter 4
3-Fluoro-N-methylcarbanilie aeid
(3-ethoxycarkonylaminophenyl) e~ter 4 4
3~1uoro-N-methylcarbanilie aeid [3-
(methylthiocarbonylamino)-phenylJ
ester 4 4
3-~luoro-N-methylcarbanilic acid [3-
(ethylthioearbonylamino)-phenyl]
e~ter 4 4
4-~luoro-N-methylearbanilie aeid (3-
ethoxyearbonylaminophenyl) ester 4 4
4-~luoro-N-(2-phenylethyl)-earbanilie
acid (3-methoxycarbonylam~nophenyl)
e~ter 4 4
4-~luoro-N-(2-phenylethyl)-earbanilie
aeid (3-ethoxyearbonylaminophenyl) ester 4 4
~-Ethyl~3-~luorocarbanilic aeid [3-
(l-me1;hylethoxycarbonylamino)-pllenyl]
~ter 4 4
N-Ethyl-4-fluoroear~anilie aeid [~
meth~letho~ye~rbonylamiIlo)-phenylJ
es~er 4 4
4-Fluoro-N-methylearbanilie aeid [3-
(l-methylethoxyearbonyla~ino)-phenyl]
e~ter 4 4
N-~thyl-4-*luoroearbanilie aeid [3-
(ethylthioearbonylamino)-phenyl3 e~ter 4 4
4-~luoro-N~methylcarbanilie aeid [3-
(ethylthiocarbonyla~ino)-phenyl] ester 4 4

8~6~
- 20 -
Com~ound o~ the invention .Solanum ra~sica
~-Fluoro~N-methylcarbanilic acid [3-
(2-propynyloxycarbonylamino)-phenyl]
ester 4 4
~-Ethyl-3-fluorocarbanilic acid [3-
(2-propynyloxycarbonylamino)-phenyl~
ester 4 4
4-Fluoro-N-(2-phenylethyl)-carbanilic
acid [~-(ethylthiocarbonylamino)-
phenyl~ e~ter 4 4
4-~luoro-N-(2-phenylethyl)-carbanilic
acid [~-(l-methylethoxycarbonylamino)-
phenylJ ester 4 4
N-Ethyl 4-~luorocarbanilic acid (~-
allylo~ycarbonylaminophenyl) e~ter 4 4
N-Ethyl-4-~luorocarbanilic acid ~3-
(2-propynylo~ycarbonylamino)-phenyl]
ester 4 4
4-~luoro-N-(2-phenylethyl)-carbanillc
acid (~-allylo2ycarbonylaminophenyl)
ester 4
3-Fluoro-N-(2-phenylethyl)-carbanilic
acid (3-methoxycarbonylaminophenyl)
ester 4 4
3-~`luoro-N-methylcarbanilio acid C3-
(l-methylethoxycarbonylamino)-phenyl]
ester 4 4
3-Fluoro-~-methylca~b~li.lic acid (3-
allylo2ycarbonylaminophenyl) e~ter 4 4
3-~.Luoro-N-ethylcarbanilic acid (3-
allylo~ycarbonylaminophenyl) e~ter 4 4
4-~luoro-N-methylcarbanilic acid (~-
allyloxycarbonylaminophenyl) e~ter 4 4
N-~thyl-3-~luorooarbanil~c acid [3-
(l-chloromethyletho2ycarbonylamino)-
phenyl] e~ter 4 4

~28~6~
- 21 -
Compound o~ the invention Solanum ~ra~ica
N-~thyl-2-~luorocarbanilic acid (3-
methoxycarbonylaminophenyl) ester 4 4
N-Ethyl-3,4-dlfluorocarbanilic acid
(3-metho~ycarbonylaminophenyl) ester 4 4
~-Fluoro-N-~2-phenylethyl)-carbanillc
acid (3-ethoxycarbonylaminophenyl)
ester , . 4 4
3-Fluoro-N-(2-phenylethyl)-carbanilic
acid [~-(ethylthiocarbonylamino)- -
phenylJ ester 4 4
3-~luoro-N-(2-phenylethyl)-carbanilic
acid C3-(ethylthiocarbonylamino)-
phenyl] ester 4
N-~thyl-3,4-di~luorocarbanilic acid
(3-ethoxycarbonylaminophenyl) e~ter 4 4
N-Ethy1-3,4-difluorocarbanilic acid
~3-(methylthiocarbonylamino)-phenyl]
ester 4 4
2-~luoro-N~(2-pheny].ethyl)-carbanilic
acid (3-methoxyc'arbonylaminophenyl)
e~ter 4 4
2-Fl~loro~N~(2-phellylethyl)-carbanilic
acid (3-ethoxycarbonylaminophenyl)
ester 4 4
2-Fluoro-N~(2-phenylethyl)-carbani~ic
acid [3~(methylthiocarbon~ylam.inG)~
phenyl~ ester 4 4
2-Fluoro-N-(2-phonylethyl)-carbanili.c
acid [~-(ethylthiocarbonylamino)-
phenylJ e~ter 4 4
2-Fluoro-N-(2-phenyleth~yl)-carbanilic
acid [~ methylethoxycarbonylamino)-
phenylJ e~ter 4 4
2-Fluoro-N-(2-phenylethyl)-carbanilic
acid [3-(2-propynyloxycarbonylamino)-
phenylJ e~ter 4 4

- ~%8Q~l
-- 2~ _
Compound o~ the invention Solanum _ras ica
N-~thyl-2-~luorocarbanilic acid (3-
etho}~ycarbon~laminophenyl) ester 4 4
N-Ethyl-2-~luorocarbanilic acid C~~
(methylthiocarbonylamino)-phenyl~
ester 4 4
N-~thyl-2-~luorocarbanilic acid [3-
(ethylthiocarbonylamino)-phenyl]
ester 4 4
N--Ethyl-2-fluorocarbanilic acid [3-
(l-methylethoxycarbonylamino)-
phenyl] e~ter 4 4
N-~thyl-2-~luorocarbanilic acid [3-
(2-propynyloxycarbonylamino)-phenyl]
ester 4 4
2-~luoro-N-(2-phenylethyl)-carba~ilic
acid (3-allyloxycarbonylaminoI)henyl)
ester 4 4
2-Fluoro-N-(2~phen~1ethyl)-carbanilic
acid [3-(2-~ethylpropoxycarbonyla~ino)-
phenylJ e~ter 4 4
¢-~luoro-N-propylcarbanilic acid (3-
~etho~ycarbonylaminophenyl) ester 4 4
4-~luoro-N-~)ropylcarbanllic acid (3-
e'~io~ycarbonylaminopll~nyl) ester 4 4
~utyl-4-~luorocarbanilic acid (3-
.ethoxycarbonyl~minophcnyl) ester 4 4
N-~u~,yl-4-~luorocarba~ilic acid (3-
e~hoxycarbonylaminophenyl) e~ter 4 4
4-~luoro-N-butylcarbanilic acid t3-
tl-methyletlloxycarbonylamino)-phenyl]
ester 4 4
4-~luoro-N-~utylcarbanilic acid [3-
(ethylthiocarbonylamino)-phenyl]
e~ter 4 4

23 -
Compound o~ the invention ~olanum ~ra~.ica
N-~utyl-4-fluorocarbanilic acid [3-
t2-propynyloxycarbonylamino)-phenyl]
ester 4 4
4-Fluoro-N-propylcarbanilic acid C3
(eth~lthiocarbonylamino)-phenyl~
ester 4 4
4-Fluoro-N-propylcarbanilic acid C3-
(2-propynyloxycarbonylamino)-phenyl]
ester 4 4
N-~utyl-4-*luorocarbanilic acid [3-
(methylthiocarbonylamino)-phenyl]
es-ter 4 4
N-~thyl-3~ orocarbaMilic acld r3-
(l-methyl-2-propenylo~ycarbonylamino)-
phenyl] ester 4 4
N-~thyl-2-~luorocar~nilic acid ~3-
(l-methyl-2-propenyloxycarbollylamin.o)-
phenyl] ester 4 4
N-Ethyl-4-fluorocarbanilic acid [3-(1-
methyl-2-propenylox~carbonylamino)-
phenyl] ester 4 ¢
N-~utyl-3-~luorocarbanilic acid (3-
metho~-ycarbon~rl~minoph~ryl) e~t~r 4 4
3-Fluoro-N-methylcarbanllic acid [3-
(2-methylpropoxycarbonylamino)-phenyl]
e~ter 4 4
4-k'luoro-N-(2~phenylethyl)-carbanilic
acid [3-(l~methyl-2-propenyloxy-
carbonylamino)-l~he~yl] ester 4 4
3-Fluoro~N-(2-phenylethyl)-carbanilic
acid C3-(1-methyl-2-propenyloxy-
carbonylamillo)-~henyl] ester 4 4
3-~luoro-N-methylcarbanilic acid ~3-
(l-methyl-2-propenyloxycarbonylamino)-
phenyl] e~ter 4 4

llZB~61
- 24 -
om~und of the invention Solanum Br~s~ica
4-~luoro-N-methylcarbanilic acid r3-
(l-methyl-2-propenyloxycarbonylamino)
phenyl~ ester 4 4
N-~utyl-4-fluorocar~)~nilic acid [3-
(l-methyl-2-propenylo~ycarbonylamino)-
phenyl] ester 4 4
4-Fluoro-N-methylcarbanilic acid [3-
(2-met~ylpropoxycarbonylamino)-phenyl]
ester 4 4
3-Fluoro-N-propylcarbanilic acid (3-
metho~ycarbonylaminophenyl) ester 4 4
3-Ptluoro-N-prop~lcarbanilic acid ~3-
(methylthiocarbonylamino)-phenyl]
ester 4 4
3-Fluoro-N-propylcarbanilic ac~d (~-
etho~ycarbonyla~inophenyl) ester 4 4
Ex~a~_~
_.,
In a se~ie~ of tests carried out in a green~louse,
the compound~ o~ the present invention listed in the
Table below were each sprayed in accordance with the
p~a-emergence method at a rate of application of 5 kg
o~ active substance per hectare, emuL~i~ied in 600 litres
o~ water per heotare, on to ~ and Solanum as the
te~t plantæ. 3 weeks after the treatment the re~ulte
thereo~ were evaluated and expressed b~y a n~nerical scale
extending from 0 to 4, the value 0 representing no action
and the value 4 repreæenting destruction of the plant.
A~ will be seen ~rom the ~'able, destruction o~ the
te~t plants wa~ achleved.

1~2~6
-- 25 _
Compound of the invention Sol~um Bra,~ica
4-~luoro-N-methylcarbanilic acid
(3-methoxycarbonylaminophenyl) ester 4 4
N-~thyl-4-~luorocarbanilic acid (~-
methoxycarbonylaminophenyl) ester 4 4
N-Ethyl-4-fluorocarb~nilic acid (3-
ethoxycarbonylaminophenyl) ester ~ 4 4
4-Fluoro-N-methylcarbanilic acid (3-
ethox~rcarbonylaminophenyl) ester 4 4
N-Ethyl-4-fluorocarbanilic acid [~-
(l-meth~lethoxycarbonylamino)-
phenyl] e~ter 4 4
Untreated
xample 4
In a ~eries of tests carried out in a greenllouse,
the plant~ listed in the Table below were treated a~ter
their emergence ~Jith the agents li~ted usin~ in each case
an application quantit~ o~ 1 ~g o~ active substance per
hectare. ~or thi~ purpose, the agent~ were in each ca~e
s~ayed unl~ormly over th~ ~lants in the ~o~m of an
emulsion, u~ing 500 litres o~ water per hectare. In
this ca~e, ~ ~eek~ ~ter the treatment thc compound~ o~
the present in~ent~on were ~ound to have high degree of
oelectivity while having an excellent action against the
weedeO The agents u~ed ~or comparison did not exhibit
this ~electivity.
~ he re~ults obt~ined are expre~sed by a numerical
scale extending from O to 10, the value O representing
total destruction o~ the ~ t and the value 10 represen-
ting no act~onO

llZ8~61
_ 26 --
BOii~OO~ O O O O
S o o o o
~wo'd'I o o o o
~n~u ë~ o o o o
~1 ~--1 r l r~l
aZ~I 'I ~ ~ ,
UO~O~ 0~ 1 0
~nu-~uno~ ~ ~o
.;
. a)
P~ t~ ~ h ~ h
. ~ ~ ~d
C) o C~ C)
cd
C~ h O h ~ h C) b~
O rl~ r~ ~ r-~ a) ~1 a
~ ~r~ ~ rl ~ r~ ~
a> .q P~
.0 -~ ,Q _ ,o _~ ,o _~
~' h rl h ~I h O h O
~: Cd P~ ~d h
.r O R C) ~ O~rl c)~,l
O Q) O O O E3 0 E~
a) h ~:: h ~ h t~ h td
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