Note: Descriptions are shown in the official language in which they were submitted.
- l - O.Z~ 0050/034525
Carbonylaminourethanes, and he.rbicides and fungicides
containing these compounds
The present in~ention relates to novel valuable
urethanes which contain a carbonylamino group, to pro- -
cesses for the preparation of these urethanes, to herbi-
cides and fungicides containing these compounds, and to
processes for controlling undesired plant growth and
fungi by means of these compounds.
The use of ethyl N-[3-(N'-phenylcarbamyloxy)-
phenyl]-carbamate and methyl N-[3-(N'-3~-methylphenyl-
carbamyloxy)-phenyl]-carbamate as herbicides is known
(German Published Application DAS 1,567,151).
It is also known that meta-(3,3-dimethylureido)-
benzyl N-(tert,-butyl)-carbamate has herbicidal proper-
ties (U.S. Patent 3,756,250),
Further, it is known that 1-[2-(2,4-dichloro-
phenyl)-2-(2-propenyloxy)-ethyl~-imidazole may be used as
a fungicide (British Patent 1,318,590),
We ha~e found that urethanes of the general form-
ula
NXCORl
Y A-O-CO-¢
R3
where
Rl is unsubstituted or halogen-, alkoxy-, alkoxy-
carbonyl- or cyano-substituted alkyl, cycloalkyl, alkenyl
or alkynyl (eg. methyl, ethyl, isopropyl, n-propyl,
9~r~
- 2 O.Z. 0050/034525
n-butyl, sec.-butyl, tert.-butyl, iso-butyl, sec.-pentyl,
chloromethyl, ,~-dichloroethyl, dichloromethyl, methoxy-
methyl, acetoxymethyl, cyanomethyl, cyclopropyl, cyclo-
hexyl, -methyl-cyclopropyl, sec.-propenyl or ethynyl)
or alkoxy (eg. methoxy, ethoxy, n-propoxy, iso-propoxy,
tert.-butoxy or sec -butoxy), cycloalkoxy (eg. cyclo-
hexoxy or cyclopentylmethoxy), alkenyloxy (eg. prcpenyl-
oxy), alkynyloxy (eg, sec -butynyloxy), cyanoalkoxy (eg,
2-cyanoethoxy), haloalkoxy (eg 2-chloroethoxy or 1,3-
difluoro-iso-propoxy), alkylthio (eg. methylthio, ethyl-
thlo, n-propylthio or tert.-butylthio), alkenylthio or
al~ynylthio,
Y is hydrogen, alkyl (eg. methyl or tert -butyl),
halogen (eg. fluorine, chlorine or bromine), alkoxy (eg.
methoxy) or haloalkyl (eg. trifluoromethyl),
A is unsubstituted or alkyl-substituted alkylene,
for example of 1 to 8 c~rbon atoms (eg. methylene, methyl-
methylene, dimethylmethylene, ethylmethylene, propylene,
hexylene, ethylene, methylethylene, methylpropylene,
ethylpropylene, methylpentylene or dimeth~lpropylene),
R2 is hydrogen, alkyl (eg, methyl, ethyl or isa-
propyl), al~oxyalkyl (eg, methoxymethyl or 2-methoxy-
ethyl), haloal~yl (eg. chloromethyl) or unsubstituted or
alkyl- or halogen-substituted benzyl,
R is alkyl which is unsubstituted or substituted
by halogen or by alkoxy or by unsubstituted or substituted
aryl (eg. methyl, ethyl, 2~chloroethyl, 2-methoxyethyl,
benzyl, isopropyl, n-propyl, 4-chlorobenzyl, n-butyl,
sec.-butyl, tert.-butyl, iso-butyl, 2,4-dichlorobenzyl,
_ 3 _ o.Z. 0050/034525
a-methyl-2-chlorobenzyl, 2-ethylhexyl or n-decyl) or is
unsubstituted or halogen-substituted alkenyl (eg allyl,
2-chloroprop-l-en-3-yl or but-1-en-3-yl), unsubstituted
or halogen- or alkoxy-substituted alkynyl (eg. propargyl,
but-l-yn-3-yl or 3 methylbut-l-yn-3-yl) or unsubstituted
or alkyl-substituted cycloalkyl (eg. cyclopentyl, cyclo-
hexyl, 3-methylcyclohexyl, 2,6-dimethylcyclohexyl, cyclo-
heptyl, 4-tert.-butylcyclohexyl, cyclooctyl, cyclododecyl
or 3,5-dimethylcyclohexyl), phenyl or monosubstituted or
polysubstituted phenyl, the substituents being alkyl,
haloalkyl~ alkoxyalkyl, cycloalkyl, halogen, alkoxy, halo-
alkoxy, nitro, aryl, aryloxy, thiocyanato, cyano,
~5 ~5
NH-C-R4, NHCooR4, NHCON , CooR4, CON , S-R4, So2R4,
d \R4 \~4
R5
oSo2R4, -Co-R4 or S02N , where R4 and R5 each indep-
R4
endently of one another are hydrogen or unsubstituted,
monosubstituted or polysubstituted aryl, or one of R4 and
R5 has one ofthe other meanings given for ~2 (~3
thus being, eg., phenyl, 4-fluorophenyl, 2-methoxyphenyl,
3-methylphenyl, 2-fluorophenyl, 3-methyl-5-iso-propyl-
phenyl, 3-ethylphenyl, 3-chlorophenyl, 2,4,~-trimethyl-
phenyl, 3-fluorophenyl, 3-chloro-4-fluorophenyl, 3,4-
dimethylphenyl, 3-trifluoromethylphenyl, 4-methylphenyl,
- 3,4-difluorophenyl, 3-chloro-4-methylphenyl, 4-bromo-
phenyl, 4-iodophenyl, 4-chlorophenyl, 2-chlorophenyl, 2-
chloro-4-fluorophenyl, 3-isopropylphenyl, 4-ethylphenyl,
5~
_ O.Z. 0050/034525
3-methoxycarbonylaminophenyl, 4-ethoxyphenyl1 2-methyl-
phenyl, 3-methoxyphenyl, 4-cyanophenyl, 2,~-dimethyl-
phenyl, 2,4-dichlorophenyl, 3-methyl-4-chlorophenyl,
- 3,4-dichlorophenyl, 3-chloro-4-bromophenyl, 3-trifluoro-
methyl-4-chlorophenyl, 3-chloro-4-difluoromethoxyphenyl 9
3-(1,1,2,2-tetrafluoroethoxy)-phenyl or 3,4-dichloro-5-
methylphenyl), exhibit a good herbicidal action on
undesired plants and are at the same time well tolerated
by crops The novel compounds furthermore have a
fungicidal action. They can therefore be used as
crop protection agents.
The novel compounds can be prepared by, for ex-
ample, the following processes:
Process I:
A hydroxy compound of the general formula
~HCORl
/ A - OH
is reacted with an isocyanate of the general formula R3-
NCO, where Rl, R3, Y and A have the above meanings; in
the novel compound produced, R2 is H. The reaction
is carried out in the presence or absence of a conven-
tional catalyst for isocyanate reactions, for example a
tertiary amine teg triethylamine or 1,4-diazabicyclo-
(2,2,2)-octane), a nitrogen-containing heterocycle (eg.
pyridine or 1,2-dimethylimidazole) or an organic tin
compound (eg. dibutyl-tin diacetate or dimethyl-tin
_ 5 _ O.Z. 0050/034525
dichloride), in the presence or absence of a solvent
which is inert under the reaction conditions, for ex-
ample a hydrocarbon (eg. naphtha, gasoline, toluene,
pentane or cyclohexane), a halohydrocarbon (eg. methylene
chloride, chloroform, dichloroethane, chlorobenzene or
o-, m- or p-dichlorobenzene), a nitrohydrocarbon (eg.
nitrobenzene or nitromethane), a nitrile (eg. aceto-
nitrile, butyronitrile or benzonitrile), an ether (eg.
diethyl ether, tetrahydrofuran or dioxane), an ester
(eg. ethyl acetate or methyl propionate), a ketone (eg.
acetone or methyl ethyl ~etone) or an amide (eg. di-
methylformamide or formamide), at from O to 150C, pre-
ferably from 40 to 100C. (S. Petersen in Methoden
der Org Chemie, volume VIII, page 131, Georg-Thieme-
Verlag, Stuttgart, 4th edition (1952)).
Process II:
An aniline of the general formula
NH2
/ ~2
A-O-CON
y " R3
where Y, A, R2 and R3 have the above meanings,is reacted
with a compound of the general formula
X - C -
O
where X is a leaving group (eg. chlorine, bromine or
Rl-C-O-) and R1 has the above meanings, in a suitable
~r~
- 6 - o.Z. 0050/034525
solvent, for example water, an alcohol (eg methanol,
ethanol or isopropanol) or one of those mentioned ~or
process I, in the presence of a conventional acid
acceptor, for example an alkali metal hydroxide, carbon-
ate or bicarbonate, an alkaline earth metal oxide,
hydroxide, carbonate or bicarbonate or a tertiary
organic base (eg, triethylamine, pyri*ine, N,N-dimethyl-
aniline, N,N-dimethylcyclohexylamine, quinoline or tri-
butylamine), at from -20 to 150C, preferably ~rom 20 to
80C (German Laid-Open Application DOS 1,643,763).
Process III:
A chlorocarbonic acid ester of the general form-
ula
NHCORl
A-OCOCl
~R2
is reacted with an amine of the general formula H-~
R3
where Rl, R2, R3, Y a~d A have the meanings gi~en above,
under the same conditions as in process II.
To prepare the hydroxy compound required in
process I, an aniline of the general formula
NH2
A - OH
_ 7 _ o.Z. 0050/034525
where Y and A have the meanings given above, is reacted
with a compound of the general formula
X - C - Rl J
O ..
where X is a leaving group (eg. chlorine, bromine or
Rl C O) and Rl has the above meanings, under the condi-
O
tions described for process II.
An anil~ne of the general formula
NH2
~ A - OH
y
where Y and A ha~e the above meanings, is obtained by
reducing a nitro compound of the general formula
N02
5~
Y
where Y has the above meanings and Z is an unsubstituted
or alkyl-substituted hydroxyalkyl, carbonylalkyl, hydroxy-
alkenyl or carbonylalkenyl radical (British Patent
758,993, and U.S. Patents 2,680,136 and 4,021,487).
The aniline required for process II is obtained
by reacting a 3-(hydroxyalkyl)-nitrobenzene with an iso-
cyanate and then reducing the nitrourethane obtained.
The chlorocarbonic acid ester employed in pro-
cess III is obtained by phosgenating one o~ the hydroxy
compounds employed in process I.
- 8 - O.Z. 0050/034525
The methods and Examples which follow illustrate
the preparation of the novel urethanes and of their
intermediates.
Method A
m-(l-Hydroxypropyl)-aniline
150 parts by weight of m-nitropropiophenone are
dissolved in 1,500 parts by volume of tetrahydrofuran
(THF), mixed with 60 parts by weight of Raney nickel and
hydrogenated in a 2.5 liter autoclave at 70C and 50 bar
hydrogen pressure, until the pressure remains constant.
The mixture is filtered, the filtrate is freed from sol-
vent and the residue is recrystallized from petroleum
ether. This gives 109 parts by weight of a compound,
of melting point 69C, which has the following structural
formula
N~2
,~
C~-OH
- - C2H5
Method B
3-(1-Hydroxyethyl)-phenylpropionamide
103 parts by weight of 3-amino--methylbenzyl
alcohol are dissolved in 600 parts by weight of THF and
84 parts by weight of NaHC03 are added. 69 4 parts
by weight of propionyl chloride are slowly added drop-
wise, the mixture is stirred overnight and is then
filtered, the solution is concentrated and the residue
is recrystallized from toluene/cyclohexane. This
_ g .. O.Z. 0050/034525
gives llO parts by weight of a ~Ihite compound, of melt-
ing point 77-79C, which has the following structural
formula: N~COC2H5
..
CH-OH
CH3
The following compounds, ~or example, can be
synthesized ~y following this procedure:
.. .
NHCOR
. A - OH
R Y Am.p.(C)
OCH3 H CH2 56- 61
OC~3 H CH(CH3)78- 80
SCH3 H CH2 77- 79
SCH3 6-CH3 CH2153-155
SCH3 H CH(CH3)121-122
C2H5 H C~2 69- 71
C2H5 H CH(C2H5)93~ 94
C2H5 H CH2CH(CH3)CH2 oil
t-C4Hg H CH2 90- 92
OC2H5 H CH2 44- 46
C~H5 4Cl CH2
Method C
0-(3-Nitrobenzyl)-N-(3,4-dichlorophenyl)-urethane
lOO parts by weight of 3-nitrobenzyl alcohol
are dissolved in 500 parts by weight of THF,. 3 drops
- 10 - O.Z. 0050/034525
of dibutyl-tin diacetate.and 123 parts by weight of
3,4- dichlorophenyl isocyanate are added, the mixture
is stirred overnight and concentrated and the residue is
stirred with toluene. The product is filtered o~f and
dried, giving 155 parts by weight of a white compound~
- of melting point 182 - 184C, which has the following
structural formula~
N02
Cl
CH20CONX~C l
A similar method may be used, for example, to
prepare 0-(3-nitrobenzyl)-N-t3-trifluoromethylphenyl)-
urethane, melting point 97-99C, and 0-(3-nitrobenzyl)-
N-(3-chlorophenyl)-urethane, melting point 123-125C
Method D
0-(3-Aminobenzyl)-N-(3,4-dichlorophenyl)-urethane
440 parts by weight of tin-II chloride are added
to a suspension of 15~ parts by wei~ht of 0-(3-nltro-
benzyl)-N-(3,4-dichlorophenyl)-urethane in 1,100 parts
by volume of alcohol and 100 parts by volume of concen-
trated hydrochloric acid, and the mixture is stirred for
4 days at 20C It is then rendered strongly alkaline
with concentrated sodium hydroxide solution, whilst being
cooled efficiently; thereafter the mixture is filtered
and the residue is repeatedly extracted by stirring with
THF. The combined THF solutions are dried and con-
centrated, and the crude product thus left is recrystal-
lized from toluene/ethyl acetate. This gives 130
~ O.Z. 005~/034525
parts by weight of white.crystals, of melting point 138-
140C, having the following structural formula:
NH2
~ CH20CONH~C1
A similar method may be used to prepare, for
example, 0-(3-aminobenzyl)-N-(3-trifluoromethylphenyl)-
urethane, which is an oil, and 0-(3-aminobenzyl)-N-~3-
chlorophenyl)-urethane, of melting point 111-113C.
Method E
N-[3-(Chlorocarbonyloxymethyl)-phenyl]-O-methylurethane
A solution of 54 parts by weight of N-(3-
hydroxymethylphenyl)-O-methylurethane and 23 7 parts by
weight of pyridine in 300 parts by volume of methylene
10. chloride is slowly added dropwise, in the course of 3
hours, to a mixture of 45 parts by weight of phosgene
and 50 parts by volume of methylene chloride at -20C.
The batch is then stirred for 2 hours at -10C, 400 ml
o~ ice water are added, and the organic phase is separ-
ated off, dried over sodium sul~ate, filtered and con-
centrated under reduced pressure at 20C. This gives
48 parts of a viscous oil which according to infrared
spectroscopy and NMR spectroscopy has the following
structure:
NHCOOCH3
C~2-0-CO-C 1
- 12 - O.Z. 0050/034525
- EXAMP~E 1
6.6 parts by weight of phenyl isocyanate and a
few drops of triethylamine are added to 10 parts by
weight of N-(3-hydroxymethylphenyl)-0-methylurethane in
100 parts by weight of THF After the mixture has
stood for two days, it is concentrated and the residue
is recrystallized from toluene. This gives 13.8
parts by weight of white crystals, of melting point 139-
141C, having the following structural formula (active
ingredient No 1)
NHCOOCH3
[~
CH20CONX~
EXAMPLE 2
24.9 parts by weight o~ 0-(3-~minobenzyl)-N-(3,4-
dichlorophenyl)-urethane aredissolved in 200 parts by
weight of THF, and 9 6 parts by weight of NaHC03, followed
~y 8 4 parts by weight of cyclopropanecarboxylic acid
chloride, are added. The mixture is stirred for 8
hours and filtered, the filtrate is concentrated and the
residue is triturated with cyclohexane and filtered off.
This gi~es 27 9 parts by weight of a compound, of melting
point 163-165C, which has the following structure
(active ingre~ient No. 2)
NHC0 ~ Cl
~ C~20CO~ Cl
- 13 - O.Z. 0050/034525
EXAMPLE 3
28 parts by weight o~ N-[3-(chlorocarbonyloxy-
methyl)-phenyl]-O-methylurethane are dissolved in 50
parts by weight of toluene. 31 g of 3-chloro-N-
methylaniline in 150 parts by weight of toluene are
added dropwise at,20C and the reaction solution is
stirred for 8 hours. It is then extracted by shaking
3 times with dilute hydrochloric acid. The solution
is then dried and concentrated, the oily residue is
caused to crystallize by means of petroleum ether, and
the product is filtered off, It consists of white
crystals of melting point 64-67C, having the following
structural formula (active ingredient No, 3)
NHCOOCH3
CH3
CH20cON~r~cI
The following compounds may be prepared analogously:
- 14 _ 0. Z. 0050/034525
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.. . - 15 - 0 . Z . 0050/034525
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- 16 - 0 . Z . 0050/034525
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--- - 17 - O.Z. 0~50/034525
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~ 18 - O.Z. 0050/034525
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- 19 - D . Z . 0050/034525
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- 20~ 30.Z. 0050/034525
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~ 21 ~ O~Z~ 0050/034525
The active ingredients may be applied as such, in the form of
formulations, or application forms prepared therefrom, e.g., as
directly sprayable solutions, powders, suspensions, dispersions,
emulsions, oil dispersions, pastes, dusts, broadcasting agents, or
granules by spraying, atomizlng, dusting, broadcast~ng or water-
ing. The forms of application depend entirely on the purpose for
which the agents are being used; in any case they should ensure as
fine a distribution of the active ingredlent as possible. The
agents generally contain from 0.1 to 95~ especially 10 to 80%
(wt%) of active ingredient.
For the preparatlon of solutions, emulsions, pastes and oil
dispersions to be sprayed direct, mineral oil fractions of medium
to high bolling point, such as kerosene or diesel oil, further
coal-tar oils, and oils of vegetable or animal origin, aliphatic,
cyclic and aromatlc hydrocarbons such as benzene, toluene, xylene,
paraffin, tetrahydronaphthalene, alkylated naphthalenes and their
derivatives such as methanol, ethanol, propanol, butanol, chloro-
form, carbon tetrachloride, cyclohexanol, cyclohexanone, chloro-
benzene, isophorone, etc., and strongly polar solvents such as
20 dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water,
etc. are suitable.
Aqueous formulations may be prepared from emulsion con-
centrates, pastes, oil dispersions or wettable powders by adding
water. To prepare emulsions, pastes and oil dispersions the ingre-
dients as such or dissolved in an oil or solvent may be homogen-
ized 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, ad-
herent, emulsifying or dispersing agent and possibly solvent or oil.
- 22 - O.Z. 0050/034525
Examples of surfactants are: alkali metal, alkaline earth
metal and ammonium salts of ligninsulfonic acid, naphthalene-
sulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl
sulfates, and alkyl sulfonates, alkali metal and alkaline earth
metal salts of dibutylnaphthalenesulfonic acid, lauryl ether
~ulfate, fatty alcohol sulfates, alkali metal and alkaline earth
metal salts of fatty aclds, salts of sulfated hexadecanols, hepta-
decanols, and octadecanols, salts of sulfated fatty alcohol glycol
ethers, condensation products of sulfonated naphthalene and
10 naphthalene derivatives with formaldehyde, condensation products
of naphthalene or naphthalenesulfonic acids with phenol and form-
aldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-
phenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkyl-
phenol polyglycol ethers, trlbutylphenyl polyglycol ethers, al~yl-
aryl polyether alcohols, isotridecyl alcohol, fatty alcohol
ethylene oxide condensates, ethoxylated castor oil, polyoxy-
ethylene 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
mixlng or grinding the active ingredients with a solid carrier.
EXAMPLE I
90 parts by weight of compound 1 is mixed with 10 parts by
weight of N-methyl-~-pyrrolidone. A mixture is obtained which is
suitable for application in the form of very fine drops.
- 23 ~ ~ ~ ~~~~ C.Z. 0~50~034525
EXAMP~E II
10 parts by weight of compound 2 is dissolved in a mixture
consistlng of 90 parts by weight o~ xylene, 6 parts by weight of
the adduct of 8 to 10 moles o~ ethylene oxide with 1 mole of oleic
acid-N-mono~thanolamide, 2 parts by weight of the calcium salt of
dodecylbenzenesulfonic acid, and 2 parts by weight of the adduct
of 40 moles of ethylene oxide with 1 mole of castor oil~
EXAMPLE III
20 parts by weight of compound 2 is dissolved in a ~ixture
10 consisting of 60 parts by weight of cyclohexanone, 30 parts by
weight of isobutanol, 5 parts by weight of the adduct of 7 moles
of ethylene oxide wlth 1 mole of isooctylphenol, and 5 parts by
weight of the adduct of 40 moles of ethylene oxide with 1 mole of
castor oil.
E~AMPLE I~
20 parts by weight of compound 3 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 and 280C, and 10 parts by weight of the adduct of 40 moles
20 of ethylene oxide with 1 mole of castor oil.
EXAMP~E V
80 parts by weight of compound 1 is well ~ixed with 3 parts
by weight of the sodium salt of diisobutylnaphthalene-~-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.
- 24 - O.Z. 0050/034525
EXAMPLE VI
5 parts by weight of compound 1 is intimately mixed with
95 parts by weight of particulate kaolin. A dust is obtained
containing 5~ by weight of the active ingredient.
EXAMPLE VII
30 parts by weight of compound 1 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 ingre-
dient is obtained having good adherence.EXAMPLE VIII
40 parts by weight of compound 1 is intimately mixed with
10 parts of the sodium salt of a phenolsulfonic acid-urea-form-
aldehyde condensate, 2 parts of silica gel and 48 parts of water.
A stable aqueous dlspersion is obtained.
EXAMPLE IX
20 parts of compound 1 is intimately mixed with 12 parts of
the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a
fatty alcohol polyglycol ether, 2 parts of the sodium salt of a
20 phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a
paraffinic mineral oil. A stable oily dispersion is obtained.
The influence of various representatives of the novel
herbicidal urethanes on the growth of unwanted and crop plants
is demonstrated in greenhouse experiments.
The vessels employed were plastic flowerpots having a volume
of 300 cm , and which were filled with a sandy loam containing
about 1.5% humus. The seeds of the test plants were sown shallow,
and separately, accordlng to species.
25 ~ O.Z. 0050/034525
In the preemergence treatment, the active ingredients were
lmmediately applied to the surface of the soil as a suspension or
emulsion in water by spraying through finely distributing nozzles.
The amount of active ingredient applied in this treatment was
equivalent to 3.0 kg/ha.
After the agents had been applied, the vessels were lightly
sprinkler-irrigated to induce germination and growth. Transparent
plastlc covers were then placed on the vessels until the plants
had taken root. The cover ensured uniform germination of the
plants, insofar as this was not impaired by the chemicals. The
comparative agent employed in this method (at the same application
rate) was m-(3,3-dimethylureido)-benzyl-N-(tert-butyl)-carbamate (A).
For the postemergence treatment, the plansts were ~irst grown
in the vessels to a height of from 3 to 10 cm, depending on growth
form, before being treated. For this treatment, either plants
whlch had been sown directly in the pots and grown there were
selected, or plants which had been grown separately as seedlings
and transplanted to the experlment vessels a few days before
treatment. ~he amount of active ingredient applied in this treat-
ment varied, depending on the active ingredient, and was either0.25, 0.5, 1.0 or 2.0 kg/ha. The comparative agents employed were
the prior art compounds methyl-N-t3-(N'-3'-methylphenylcarbamoyl-
oxy)-phenyl]-carbamate (B) at 0.25, 0.5 and 1.0 kg/ha, and
ethyl-N-[3-(N'-phenylcarbamoyloxy)-phenyl]-carbamate (C) at
2.0 kg/ha.
No cover was placed on the vessels. The pots were set up in
the greenhouse - species from warmer areas at from 20 to 35 C,
- 26 - O.Z. 0050/034525
and species from moderate climates at 10 to 25C. The experiments
were run for from 2 to 4 weeks. During this period, the plants
were tended and their reactions to the various treatments asses-
sed. The scale used for assessment was 0 to 100, 0 denoting no
damage or normal emergence, and lO0 denoting nonemergence or
complete destruction of at least the visible plant parts.
The results show that the novel compounds have, on postemer-
gence application, a better herbicidal action than the comparative
agents on a number of unwanted plants. In addition, a number of
10 compounds according to the invention are better tolerated by
certaln crop plants than the comparative agentsO When the novel
compounds are applied preemergence, a herbicidal action is also
observed.
If the crop plants tolerate the active ingredients less well~
appllcatlon technlques may be used in which the agents are sprayed
frrom sultable equipment ln such a manner that the leaves of
sensitive crop plants are if possible not touched, and the agents
reach the soil or the unwanted plants growing beneath the crop
plants (post-directed, lay-by treatment).
In view of the good tolerance of the active ~ngredients and
the many application methods posslble, the agents accord~ng to the
invention, or mixtures containing them, may be used not only on
the crop plants listed in Table 1, but also in a much larger range
of crops for removing unwanted plants.
The followlng crop plants may be mentloned by way o~ example:
- 27 - O.Z. 0050/034525
Botanical name Common name
Allium cepa onions
Ananas comosus pineapples
Arachis hypogaea peanuts (groundnuts)
Asparagus officinalis asparagus
Avena sativa oats
Beta vulgaris spp. altissima sugarbeets
Beta vulgarls spp. rapa fodder beets
Beta vulgaris spp. esculenta table beets, red beets
10 Brassica napus var. napus rape
Brassica napus var. napobrassica
Brasslca napus var. rapa turnips
Brassica rapa var. silvestris
Camellia sinensis tea plants
Carthamus tinctorius safflower
Carya illinoinensis pecan trees
Citrus limon lemons
Citrus maxlma grapefruits
Citrus reticulata mandarins
20 Citrus sinensis orange trees
Coffea arabica (Coffea canephoral
Coffea liberica) coffee plants
Cucumis melo melons
Cucumis sativus cucumbers
Cynodon dactylon Bermudagrass in turf and lawns
Daucus carota carrots
Elais guineensis oil palms
Fragaria vesca strawberries
`- 28 - ~ O.Z. 0050~034525
~otanical name Common name
_ _ _ . _ _
Glycine max soybeans
Gossypium hirsutum
(Gossypium arboreum cotton
Gossypium herbaceum
Gossypium vitifolium)
Helianthus annuus sunflowers
Helianthus tuberosus
Hevea brasiliensis rubber plants
Hordeum vulgare barley
Humulus lupulus hops
Ipomoea batatas sweet potatoes
Juglans regia walnut trees
Lactuca sativa lettuce
Lens culinaris lentils
Linum usitatlssimum flax
Lycopersicon lycopersicum tomatoes
Malus spp. apple trees
Manihot esculenta cassava
Medicago sativa alfalfa (lucerne)
Mentha piperita peppermint
Musa spp. banana plants
Nicothiana tabacum tobacco
(N. rustica)
Olea europaea olive trees
Oryza sativa rice
Panicum miliaceum
Phaseolus lunatus limabeans
Phaseolus mungo mungbeans
Phaseolus vulgaris snapbeans, green beans,
dry beans
Pennisetum glaucu~
Petroselinum crispum parsley
spp. tuberosum
3B~
- 2 - O.Z. 0050/034525
30tanical name Common name
... . . _ _
Picea abies Norway spruce
Abies alba fir trees
Pinus spp. pine trees
Pisum sativum English peas
Prunus avium cherry trees
Prunus domestica plum tree,s
Prunus dulcis almond trees
Prunus persica peach trees
10 Pyrus communis pear trees
Ribes sylvestre redcurrants
Ribes uva-crispa gooseberries
Ricinus communis castor-oil plants
Saccharum officinarum sugar cane
Secale cereale rye
Sesamum indicum sesame
Solanum tuberosum Irish potatoes
Sorghum bicolor (s. vulgare) sorghum
Sorghum dochna
20 Spinacia oleracea spinach
Theobroma cacao cacao plants
Tri~olium pratense red clover
Triticum aestivum wheat
Vaccinium corymbosum blueberries
Vaccinium vitis-idaea cranberries
Vicia faba tick beans
Vigna sinensis (V. unguiculata) cow peas
Vitis vinifera grapes
Zea mays Indian corn, sweet corn, maize
- 30 - O.Z. 0050/034525
To increase the spectrum o~ action and to achieve synergistic
effects~ the novel urethanes may be mixed and applied together
with numerous representatives of other herbicidal or growth-
-regulating active ingredient groups. Examples of suitable
mixture components are diazines, 4H-3,1-benzoxazine derivatives,
benzothiadiazinones, 2,6-dinitroanilines, N-phenyl~ carbamates,
thiolcarbamates, halocarboxyllc acids, trlazines, amides, ureas,
dlphenyl ethers, triazinones, uracils, benzofuran derivatives,
cyclohexane-1,3-dione derivatives, etc. A number of active ingre-
10 dients which, when combined with the new compounds, give mixturesuseful for widely varying applications are given below by way of
example:
5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone
5-amino-4-bromo-2-phenyl-3(2H)-pyridazinone
5-amino-4-chloro-2-cyclohexyl-3(2H)-pyridazinone
5-amino-4-bromo-2-cyclohexyl-3(2H)-pyridazinone
5-methylamlno-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-
20 -pyridazinone
5-methylamino-4-chloro-2-(3-d,~ -tetrafluoroethoxyphenyl)-
-3(2H)-pyridazinone
5-dimethylamino-4-chloro-2-phenyl-3(2H)-pyridazinone
4,5-dimethoxy-2-phenyl-3(2H)-pyridazinone
4,5-dimethoxy-2-cyclohexyl-3(2H)-pyridazinone
4,5-dimethoxy-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone
5-methoxy-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone
5-amino-4-bromo-2(3-methylphenyl)-3(2H)-pyridazinone
- 31 - O.Z. 0050/034525
3~ methylethyl)-lH-2,1,3-benzothiadlazin-4(3H)-one-2,2-dioxide
and salts
3-(1-methylethyl)-8-chloro-lH-2,1,3-benzothiadiazin-4(3H)-one-
-2,2-dioxide and salts
3-(1-methylethyl)-8-fluoro-lH-2,1,3-benzothiadiazin-4(3H)-one-
-2,2-dioxide and salts
3-(1-methylethyl)-8-methyl-lH-2,1,3-benzothiadiazin-4(3H)-one-
-2,2-dioxide and salts
l-methoxymethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
-one-2,2-dioxide
l-methoxymethyl-8-chloro-3-(1-methylethyl)-2,1,3-benzothia-
diazin-4(3H)-one-2,2-dioxide
l-methoxymethyl-8-fluoro-3-(1-methylethyl)-2,1,3-benzothiadiazin-
-4(3H)-one-2,2-dioxide
l-cyano-8 chloro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
-one-2,2-dioxide
l-cyano-8-fluoro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
-one-2,2-dioxide
l-cyano-8-methyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
-one-2~2-dioxide
l-cyano-3-(1-methylethyl)-2,1,3-benzothladiazln-4(3H)-one-2,2-
-dioxide
l-azidomethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
-one-2,2-dioxide
3-(1-methylethyl)-lH-pyridino-~3,2-e]-2,1,3-thiadiazin-(4)-one-
-2,2-dioxide
A~ ~ 3
- 32 - O.Z. 0050/034525
N-(1-ethylpropyl)-2,6-dinitro-3,LI-dimethylaniline
N-(1-methylethyl)-N-ethyl-2,6-dinitro-4-trifluoromethylaniline
N-n-propyl-N-R-chloroethyl-2,6-dinitro-4-trifluoromethyl-
aniline
N-n-propyl-N-cyclopropylmethyl-2,6-dinitro-4-trifluoromethyl-
aniline
N-bis-(n-propyl)-2,6-dinitro-3-amino-4-trifluoromethylaniline
N-bis-(n-propyl)-2,6-dinitro-4-methylaniline
N-bis-(n-propyl)-2,6-dinitro-4-methylsulfonylaniline
10 N-bi 9- ( n-propyl)-2,6-dinitro-4-aminosulfonylaniline
bis-(~-chloroethyl)-2,6-dinitro-4-methylaniline
N-ethyl-N-(2-methylallyl)-2,6-dinitro-4-trifluoromethylaniline
3,4-dichlorobenzyl N-methylcarbamate
2,6-di-tert.butyl-4-methylphenyl N-methylcarbamate
isopropyl N-phenylcarbamate
3-methoxyprop-2-yl N-3-fluorophenylcarbamate
isopropyl N-3-chlorophenylcarbamate
but-1-yn-3-yl N-3-chlorophenylcarbamate
20 4-chlorobut-2-yn-1-yl N-3-chlorophenylcarbamate
methyl N-3,4-dichlorophenylcarbamate
methyl N-(4-aminobenzenesulfonyl)-carbamate
0-(N-phenylcarbamoyl)-propanone oxime
N-ethyl-2-(phenylcarbamoyl)-oxypropionic acid amide
3'-N-isopropylcarbamoyloxypropionanilide
ethyl-N-(3-(N'-phenylcarbamoyloxy)-phenyl)-carbamate
methyl-N-(3-(N'-methyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate
- 33 - O.Z. 0050/034525
isopropyl-N-(3-(N'-ethyl-N'-phenylcarbamoyloxy)-phenyl)-
-carbamate
methyl-N-(3-(N'-3-methylphenylcarbamoyloxy)-phenyl)-carbamate
methyl-N-(3-(N'-4-fluorophenylcarbamoyloxy)-phenyl)-carbamate
methyl-N-(3-(N'-3-chloro-4-fluorophenylcarbamoyloxy)-phenyl)-
-carbamate
ethyl-N-t3-N'-(3-chloro-4-fluorophenylcarbamoxyloxy)-phenyl~-
-carbamate
ethyl-N-[3-Nr-(3~4-di~luorophenylcarbamoyloxy)-phenyl]-carbamate
methyl-N-~3-(N'-3,4-difluorophenylcarbamoyloxy)-phenyl]-carbamate
methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylcarbamate
ethyl N-3-(2'-methylphenoxycarbonylamlno)-phenylcarbamate
methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylthiolcarbamate
methyl N-3-(2',4',5'-trimethylphenoxycarbonylamino)-phenylthiol-
carbamate
methyl N-3-(phenoxycarbonylamino)-phenylthiolcarbamate
p-chlorobenzyl N,N-dlethylthiolcarbamate
ethyl N,N-di-n-propylthiolcarbamate
n-propyl N,N-di-n-propylthiolcarbamate
2,3-dichloroallyl N,N-diisopropylthiolcarbamate
2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate
3-methyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate
3-ethyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate
ethyl N,N-di-sec.-butylthiolcarbamate
34 O.Z. 0050/034525
benzyl N,N-di-sec.-butylthiolcarbamate
ethyl N-ethyl-N-cyclohexylthiolcarbamate
ethyl N-ethyl-N-bicyclo-~2.1.1]-heptylthiolcarbamate
S-(2,3-dichloroallyl)-(2,2,4-trimethylazetidine)-1-carbothiolate
S-(2,3,3-trichloroallyl) (2,2,4-trimethylazetidlne)-1-carbothiolate
S-ethylhexahydro-1-H-azepine-l-carbothiolate
S-benzyl-(3-methylhexahydro-1-H-azepine-l)-carbothiolate
S-benzyl-(2,3-dimethylhexahydro-1-H-azepine-l)-carbothiolate
S-ethyl-(3-methylhexahydro-1-H-azepine-l)-carbothlolate
n-propyl N-ethyl-N-n-butylthiolcarbamate
2-chloroallyl N,N-dimethyldithiocarbamate
N-methyldithlocarbamic acld, sodium salt
trichloroacetlc acid, sodium salt
~,~-dichloropropionic acid, sodium salt
~,~-dichlorobutyric acid, sodium salt
-tetrafluoropropionic acid, sodium salt
~-methyl-~,~-dichloropropionic acid, sodium salt
methyl~ -chloro-~-(4-chlorophenyl)-propionate
20 methyl ~,R-dichloro-~-phenylpropionate
benzamido oxyacet~c acid
2,3,5-triiodobenzoic acid (salts, esters, amides)
2,3,6-trichlorobenzolc acid ~salts, esters, amides)
2,3,5,6-tetrachlorobenzoic acid (salts, esters, amides)
2-methoxy-3,6-dichlorobenzoic acid (salts, esters, amides)
2-methoxy-3,5,6-trichlorobenzoic acid tsalts, esters, amides)
3-amino-2,5,6-trichlorobenzoic acid (salts, esters, amides)
0,S-dimethyltetrachlorothioterephthalate
35 - O.Z. 0050/034525
dimethyl-2,3,5,6-tetrachloroterephthalate
dlsodium 3,6-endoxohexahydrophthalate
4-amlno-3,5,6-trichloropicolinic acid (salts)
ethyl 2-cyano-3-(N-methyl-N-phenyl)-aminoacrylate
isobutyl 2-~4-(4'-chlorophenoxy)-phenoxy]-propionate
methyl 2-~4-(2',4'-dichlorophenoxy)-phenoxy]-propionate
methyl 2-~4-(4'-tri~luoromethylphenoxy)-phenoxy]-propionate
2-~4-(2'-chloro-4'-trifluorophenoxy)-phenoxy]-propionic acid,
sodium salt
2-~4-(3',5'-dichloropyridyl-2-oxy)-phenoxy]-propionic acid,
sodium salt
ethyl 2-(M-benzoyl-3,4-dichlorophenylamino)-propionate
methyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate
isopropyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate
2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine
2-chloro-4-ethylamino-6-(amino-2'-propionitrile)-1,3,5-triazine
2-chloro-4-ethylamino-6-(2-methoxypropyl)-2-amino-1,3,5-
-triazine
2-chloro-4-ethylamino-6-butyn-1-yl-2-amino-1,3,5-triazine
2-chloro-4,6-bisethylamino-1,3,5-triazine
2-chloro-4,6-bisisopropylamino-1,3,5-triazine
2-chloro-4-isopropylamino-6-cyclopropylamino-1,3,5-triazine
2-azido-4-methylamino-6-isopropylamino-1,3,5-triazine
2-methylthio-4-ethylamino-6-isopropylamino-1,3,5-triazine
2-methylthio-4-ethylamino-6-tert.butylamino-1,3,5-triazine
4~
.
- 36 - O.Z. 0050/034525
2-methylthio-4,6-bisethylamino-1,3,5-triazlne
2-methylthio-4,6-bisisopropylamino-1,3,5-triazine
2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine
2-methoxy-4,6-bisethylamino-1,3,5-triazine
2-methoxy-4,6-bisisopropylamino-1,3,5-triazine
4-amino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one
4-amlno-6-phenyl-3-methyl-4,5-dihydro-1,2,4-triazin-5-one
lO 4-isobutylidenamino-6-tert.butyl-3-methylthio-4,5-dihydro_1,2,4_
-triazin-5-one
l-methyl-3-cyclohexyl-6-dimethylamino-1,3,5-triazin-2,4-dione
3-tert.butyl-5-chloro-6-methyluracil
3-tert.butyl-5-bromo-6-methyluracil
3-lsopropyl-5-bromo-6-methyluracil
3-sec.butyl-5-bromo-6-methyluracil
3-(2-tetrahydropyranyl)-5-chloro-6-methyluracll
3-(2-tetrahydropyranyl)-5,6-trimethyleneuracil
20 3-cyclohexyl-5,6-trimethyleneuracil
2-methyl-4-(3'-trifluoromethylphenyl)-tetrahydro-1,2,4-oxa-
diazine-3,5-dione
2-methyl-4-(4'-fluorophenyl)-tetrahydro-1,2,4-oxadiazine-3,5-
-dione
3-amino-1,2,4-triazole
l-allyloxy-1-(4-bromophenyl)-2-tl',2',4'-triazolyl-(l')]-
-ethane (salts)
1-(4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,3-triazol-1-yl)-
30 -butan-2-one
- 37 - O.Z. 0050/034525
N,N-diallylchloroacetamide
N-isopropyl-2-chloroacetanilide
N-(l-methylpropy~n-2-yl)-2-chloroacetanilide
2-methyl-6-ethyl-N-propargyl-2-chloroacetanilide
2-methyl-6-ethyl-N-ethoxymethyl-2-chloroacetanilide
2-methyl-6-ethyl-N-(2-methoxy-1-methylethyl)-2-chloroacetanilide
2~methyl-6-ethyl-N-(isopropoxycarbonylethyl)-2-chloroacetanilide
2-methyl-6-ethyl-N-(4-methoxypyrazol~l-yl-methyl)-2-chloro-
10 -acetanilide
2-methyl-6-ethyl-N-(pyrazol-l-yl-methyl)-2-chloroacetanilide
2,6-dimethyl-N-(pyrazon-l-yl-methyl)-2-chloroacetanilide
2,6-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-2-chloro-acetanilide
2,6-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-2-chloroacetanilide
2,6-dimethyl-N-(3,5-dimethylpyra~ol-1-yl-methyl)-2-chloro-
acetanilide
2,6-dimethyl-N-(1,3-dioxolan-2-yl-methyl)-2-chloroacetanllide
2,6-dimethyl-N-(2-methoxyethyl)-2-chloroacetanilide
2,6-dimethyl-N-isobutoxymethyl-2-chloroacetanilide
2,6-diethyl-N-methoxymethyl-2-chloroacetanil~de
2,6-diethyl-N-n-butoxymethyl-2-chloroacetanilide
2,6-diethyl-N-ethoxycarbonylmethyl-2-chloroacetanilide
2,3,6-trimethyl-N-(pyrazol-l-yl-methyl)-2-chloroacetanilide
2,3-dimethyl-N-isopropyl-2-chloroacetanilide
2,6-diethyl-N-(propoxyethyl)-2-chloroacetanilide
38 - O.Z. 0050/034525
2-(2-methyl-4-chlorophenoxy-N-methoxyacetamide
2-( -naphthoxy)-N,N-diethylpropionamide
2,2-diphenyl-N,N-dimethylacetamide
~-(3,4,5-tribromopyrazol-1-yl)-N,N-dimethylpropionamide
N-(l,l-dimethylpropynyl)-3,5-dichlorobenzamide
N-l-naphthylphthalamic acid
propionic acid 3~4-dichloroanilide -
cyclopropanecarboxylic acid 3,4-dichloroanilide
methacrylic acid 3,4-dichloroanilide
2-methylpentanecarboxylic acid 3,4-dichloroanilide
5-acetamido-2,4-dimethyltrifluoromethanesulfone anilide
5-acetamido-4-methyltrifluoromethanesulfone anilide
2-propionylamino-4-methyl-5-chlorothiazole
0-(methylsulfonyl)-glycolic acid N-ethoxymethyl-2,6-dimethyl-
anilide
0-(methylaminosulfonyl)-glycolic acid N-isopropylanilide
0-(isopropylaminosulfonyl)-glycolic acid N-but-l-yn-3-yl-anilide
0-(methylaminosulfonyl)-glycolic acid hexamethyleneamide
2,6-dichlorothiobenzamlde
2,6-dichlorobenzonitrile
3,5-dibromo-4-hydroxybenzonitrile (salts)
3,5-diiodo-4-hydroxybenzonitrlle (salts)
3,5-dibromo-4-hydroxy-0-2,4-dinitrophenylbenzaldoxime (salts)
3,5-dibromo-4-hydroxy-0-2-cyano-4-nitrophenylbenzaldoxime
(salts)
pentachlorophenol, sodium salt
- 39 - O.Z. 0050/034525
2,4-dichlorophenyl-4'-nitrophenyl ether
2,4,6-trichlorophenyl-4'-nitrophenyl ether
2-fluoro-4,6-dichlorophenyl-4'-nitrophenyl ether
2-chloro-4-trifluoromethylphenyl-4'-nitrophenyl ether
2,4'-dlnitro-4-trifluoromethyl-diphenyl ether
2,4-dichlorophenyl-3'-methoxy-4'-nitro-phenyl ether
2-chloro-4-trifluoromethylphenyl-3'-ethoxy-4'-nitro-phenyl ether
2-chloro-4-trifluoromethylphenyl-3'-carboxy-4'-nitro-phenyl
ether (~alts)
10 2,4-dichlorophenyl-3'-methoxycarbonyl 4'-nitro-phenyl ether
2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione
2-(3-tert.butylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-
-3,5-dione
2-(3-lsopropylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-
-3,5-dlone
2-phenyl-3,1-benzoxazinone-(4)
(4-bromophenyl)-3,4,5,9,10-pentaazatetracyclo-t5,4,1,02'6'0,8'11]-
-dodeca-3,9-diene
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethane sulfonate
20 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzo~uranyldimethylamino-
sulfate
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl-(N-methyl-N-
-acetyl)-amlnosulfonate
3,4-dichloro-1,2-benzisothiazole
N-4-chlorophenyl-allylsuccinimide
2-methyl-4,6-dinitrophenol (salts, esters)
2-sec.butyl-4,6-dinitrophenol (salts, esters)
2-sec.butyl-4,6-dinitrophenol acetate
.r~ 3
- 40 - O.Z. 0050/034525
2-tert.butyl-4,6-dinitrophenol acetate
2-tert.butyl-4,6-dinitrophenol (salts)
2-tert.butyl-5-methyl-4,6-dinitrophenol (salts)
2-tert.butyl-5-methyl-4,6-dinitrophenol acetate
2-sec.amyl-4,6-dinltrophenol (salts, esters)
1-(~,~-dimethylbenzyl)-3-(4-methylphenyl)-urea
l-phenyl-3-(2-methylcyclohexyl)-urea
10 1-phenyl-1-benzoyl-3,3-dimethylurea
1-(4-chlorophenyl)-1-benzoyl-3,3-dimethylurea
1-(4-chlorophenyl)-3,3-dimethylurea
1-(4-chlorophenyl)-3-methyl-3-but-1-yn-3-yl-urea
1-(3,4-dichlorophenyl)-3,3-dtmethylurea
1-(3,4-dichlorophenyl)-1-benzoyl-3,3-dimethylurea
1-(3,4-dichlorophenyl)-3-methyl-3-n.butylurea
1-(4-lsopropylphenyl)-3,3-dimethylurea
1-(3-trifluoromethylphenyl)-3,3-dimethylurea
l-(~,~,~,~-tetrafluoroethoxyphenyl)-3,3-dimethylurea
1-(3-tert.butylcarbamoyloxyphenyl)-3,3-dimethylurea
1-(3-chloro-4-methylphenyl)-3,3-dimethylurea
1-(3-chloro-4-metho~yphenyl)-3,3-dimethylurea
1-(3,5-dichloro-4-methoxyphenyl)-3,3-dimethylurea
1-~4-(4'-chlorophenoxy)-phenyl]-3,3-dimethylurea
1-~4-(4'-methoxyphenoxy)-phenyl]-3,3-dimethylurea
l-cyclooctyl-3,3-dimethylurea
l-(hexahydro-4,7-methanoindan-5-yl)-3,3-dimethylurea
1-~1- or 2-(3a,4,5,7,7a-hexahydro)-4,7-methanoindanyl]-3,3-di-
30 methylurea
- 41 - O.Z. 0050/034525
1-(4-fluorophenyl)-3-carboxymethoxy-3-methylurea
l-phenyl-3-methyl-3-methoxyurea
l-(4-chlorophenyl)-3-methyl-3-methoxyurea
1-(4-bromophenyl)-3-methyl-3-methoxyurea
1-(3,4-dichlorophenyl)-3-methyl-3-methoxyurea
1-(3-chloro-4-bromophenyl)-3-methyl-3-methoxyurea
1-(3-chloro-4-isopropylphenyl)-3-methyl-3-methoxyurea
1-(3-chloro-4-methoxyphenyl)-3-methyl-3-methoxyurea
1-(3-tert.butylphenyl)-3-methyl-3-methoxyurea
10 1-(2-benzthiazolyl)-1,3-dimethylurea
1-(2-benzthiazolyl)-3-methylurea
1-(5-trifluoromethyl-1,3,4-thiadiazolyl)-1,3-dimethylurea
imldazolidin-2-one-1-carboxylic acid isobutylamlde
1,2-dimethyl-3,5-diphenylpyrazolium-methylsulfate
1,2,4-trimethyl-3,5-diphenylpyrazolium-methylsulfate
1,2-dimethyl-4-bromo-3,5-diphenylpyrazolium-methylsulfate
1,3-dimethyl-4-(3,4-dichlorobenzoyl)-5-(4-methylphenylsulfonyloxy)-
-pyrazole
2,3,5-trichloropyrldlnol-(4)
- 20
l-methyl-3-phenyl-5-(3'-trifluoromethylphenyl)-pyridone-(4)
l-methyl-4-phenylpyridinium chloride
l,l-dimethylpyridinium chloride
3-phenyl-4-hydroxy-6-chloropyridazine
1,1'-dimethyl-4,4'-dipyridylium-di(methylsulfate)
1,1'-di-(3,5-dimethylmorpholine-carbonylmethyl)-4,4'-dipyridylium
dichloride
1,1'-ethylene-2,2'-dipyridylium dibromide
- 42 - O.Z. 0050/034525
3-[1-(N-ethoxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-
-2,4-dione
3-~1-(N-allyloxyamino)-propylidene~-6-ethyl-3,4-dihydro-2H-pyran-
-2,4-dione
2-tl-(N-allyloxyamino)-propylidene]-5,5-dimethylcyclohexane-1,3-
-dione (salts)
2-~1-(N-allyloxyamino-butylidene]-5,5-dimethylcyclohexane-1,3-
-dione (salts)
2-~1-(N-allyloxyamino-butylidene]-5,5-dimethyl-4-methoxycarbonyl-
10 -cyclohexane-1,3-dione (salts)
2-chlorophenoxyacetic acld (salts, esters, amides)
4-chlorophenoxyacetlc acld (salts, esters, amides)
2,4-dichlorophenoxyacetic acid (salts, esters, amides)
2,4,5-trichlorophenoxyacetic acid (salts, esters, amides)
2-methyl-4-chlorophenoxyacetic acid (salts, esters, amides)
3,5,6-trichloro-2-pyridinyl-oxyacetic
acid (salts, esters, amides)
methyl ~-naphthoxyacetate
2-(2-methylphenoxy)-propionic acid (salts, esters, amides)
20 2-(4-chlorophenoxy)-propionic acid (salts, esters, amldes)
2-(2,4-dichlorophenoxy)-propionic acid (salts, esters, amides)
2-(2,4,5-trichlorophenoxy)-propionic acid (salts, esters, amides)
2-(2-methyl-4-chlorophenoxy)-propionic acid (salts, esters, amides)
4-(2,4-dichlorophenoxy)-butyric acid (salts, esters, amides)
4-(2-methyl-4-chlorophenoxy)-butyric acid (salts, esters, amides)
cyclohexyl-3-(2,4-dichlorophenoxy)-acrylate
9-'nydroxyfluorenecarboxylic acid-(9) (salts, esters)
2,3,6-trichlorophenylacetic acid (salts, esters)
4-chloro-2-oxobenzothiazolin-3-yl-acetic acid (salts, esters)
~als~3
- 43 - O.Z. 0050/034525
gibelleric acid (salts)
disodium methylarsonate
monosodium salt of methylarsonic acid
M-phosphonomethyl-glycine (salts)
N,N-bis-(phosphonomethyl)-glycine (salts)
2-chloroethyl 2-chloroethanephosphonate
ammonium-ethyl-carbamoyl-phosphonate
dl-n-butyl-l-n-butylamino-cyclohexyl-phosphonate
trlthiobutylphosphlte
10 0,0-diisopropyl-5-(2-benzosul~onylaminoethyl)-phosphorodithionate
2,3-dihydro-5/6-dimethyl-1,4-dithiin-1,1,4,4-tetraoxide
5-tert.butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxa-
diazolone-(2)
4,5-dichloro-2-trifluoromethylbenzimldazole (salts)
1,2,3,6-tetrahydropyrldazlne-3,6-dione (salts)
succinic acid mono-N-dimethylhydrazide (salts)
(2-chloroethyl)-trlmethylammonium chloride
(2-methyl-4-phenylsulfonyl)-trifluoromethanesul~one anilide
1,1-dimethyl-4,6-diisopropyl-5-indanyl ethyl ketone
20 sodium chlorate
ammonium thiocyanate
calcium cyanamide
2-chloro-4-trifluoromethyl-3'-ethoxycarbonyl-4'-nitrophenyl
ether
1-(4-benzyloxyphenyl)-3-methyl-3-methoxyurea
2-tl-(2,5-dimethylphenyl)-ethylsul~onyl]-pyridine-N-oxide
l-acetyl-3-anilino-4-methoxycarbonyl-5-methylpyrazole
~&;9~t~3
- 44 - O.Z. 005~/034525
3-anilino-4-methoxycarbonyl-5-methylpyrazole
3-tert.butylamino-4-methoxycarbonyl-5-methylpyrazole
N-benzyl-N-isopropyl-trimethylacetamide
methyl 2-[4-(4'-chlorophenoxymethyl)-phenoxy]-propionate
methyl 2-t4-(5'-bromopyridyl-2-oxy)-phenoxy]-propionate
methyl 2-t4-(5'-iodopyridyl-2-oxy)-phenoxy]-propionate
n-butyl 2-t4-(5'-iodopyridyl-2-oxy)-phenoxy~-propionate
2-chloro-4-trlfluoromethylphenyl-3'-(2-fluoroethoxy)-4'-nitro-
phenyl ether
lO 2-chloro-4-trifluoromethylphenyl-3 (ethoxycarbonyl)-methyl-
thlo-4-nitrophenyl ether
2,4,6-trlchlorophenyl-3(ethoxycarbonyl)-methylthio-4-nitro-
phenyl ether
2-tl-(N-ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-3-
-hydroxy-cyclohex-2-en-1-one (salts)
2-tl-(N-ethoxamino)-butylidene]-5-(2-phenylthiopropyl)-3-
-hydroxy-cyclohex-2-en-1-one (salt 3 )
ethyl 4-t4-(4'-trifluoromethyl)-phenoxy]-pentene-2-carboxylate
20 2-chloro-4-trifluoromethyl-3'-methoxycarbonyl-4'-nitrophenyl
ether
2,4-dichlorophenyl-3'-carboxy-4'-nitrophenyl ether (salts)
4,5-dimethoxy-2-(3-~ trifluoro-~-oromoethoxyphenyl)-3-
-(2H)~pyridazinone
2,4-dichlorophenyl-3'-ethoxy-ethoxy-ethoxy-4'-nitrophenyl ether
2,3-dihydro-3~3-dimethyl-5-benzofuranyl-ethane sulfonate
N-t4-methoxy-6-methyl-1,3,5-triazin-2-yl-aminocarbonyl]-
-2-chlorobenzene sulfonamide
1(3-chloro-4-ethoxyphenyl)-3,3-dimethylurea
45 ~ 3 o . Z ~ 0050/034525
ethyl 2-methyl-4-chlorophenoxy-thioacetate
2-chloro-3,5-diiodo-4-acetoxy-pyridine
1(-4-~2-(4-methylphenyl)-ethoxy]-phenyl-3-methyl-3-methoxyurea.
In investigations into the herbicidal action on preemergence
application in the greenhouse at a rate of 3.0 kg of active ingre-
dient per hectare, new compounds nos. 76, 94, 36 and 98 were
better tolerated by crop plants than prior art active
ingredient A.
In investigations lnto selective herbicidal action on ~ost-
10 emergence application in the greenhouse, active ingredient no. 109has a better herbicidal action at 0.5 kg/ha, no. 123 at 0.5 g/ha,
no. 90 at 1.0 kg/ha and no. 63 at 0.5 kg/ha, and, in particular,
are better tolerated by crop plants than prior art active ingre-
dient B at 0.5 o r 1.0 kg/ha.
In selective weed control on postemergence treatment in the
greenhouse, active ingredients nos. 13 and 14 have, at 0.25 kg/ha,
a better herbicidal and selective action than prior art active
ingredient B at 0.25 kg/ha.
New compounds nos. 108 and 121 also have, at l.0 kg/ha and on
20 postemergence application in the greenhouse, a much better her-
bicidal action than prior art active ingredient B.
In investigations into the selective herbicidal action on
postemergence application in the greenhouse, active ingredient
no. 88 is, at 2.0 kg/ha, better tolerated than prior art active
ingredient C.
In investigations into the herbicidal action on postemergence
application in the greenhouse at 2 kg o~ active ingredient per
hectare, compound no. 36 exhibited a good herbicidal action.
- 46 - O.Z. 0050/034525
In investigations into the herbicidal action on postemergence
application in the greenhouse at 1 kg of active ingredient per
hectare, compounds nos. 109 and 114 exhibited a good herbicidal
action.
In investigations into the herbicidal action on postemergence
application in the greenhouse at 2 kg of active ingredient per
hectare, compounds nos. 47 and 62 exhibit~ed a good herblcidal
action.
In investigations into the herbicidal action on postemergence
10 application in the greenhouse at 0.5 kg of active ingredient per
hectare, compounds nos. 101, 63 and 107 exhibited a good
herbicidal action.
Table 1 List of plant names
Botanical name Abbreviation in tables Common name
Abutilon theophrasti Abutilon theoph. velvet leaf
- Amaranthus spp. - pigweed
Arachys hypogaea Arachys hypog. peanuts
Avena sativa - oats
20 Euphorbia genlculata - South American
member of the
spurge family
Gossypium hirsutum - cotton
Hordeum vulgare - barley
Mercurialis annua - annual mercury
Sinapis alba - white mustard
Solanum nigrum - black nightshade
Triticum aestivum - wheat
_ _ _
~ 8 ~ 3
- 47 - O.Z. 0050/034525
The novel active ingredients have a strong fungitoxlc action
on phytopathogenic fungi, especially from the Ascomycetes class.
The following fungi may be mentioned by way of example: Erysiphe
graminis in wheat, Erysiphe cichoriacearum in cucumbers, Uncinula
necator in grapes, and Podosphaera leucotrichia in apples.
When the novel compounds are employed to protect crop plants,
the fungicidal agents contain from 0.1 to 95J and preferably from
0.5 to 90, % (wt%) of active lngredient. The application rates
depend on the type of effect desired, and range from 0.01 to 3 kg
10 and more of active ingredient per hectare, but are preferably from
0.01 to 1 kg/ha.
The active ingredients according to the invention may also be
mixed with other, prior art; fungicides. In many cases, the
spectrum of fungicidal action is increased; with a number of these
fungicidal compositlons, synergistic effects also occur, i.e., the
fungicidal action of the comblnation product is greater than the
effect of the individual components added together.
Examples of fungicides which may be combined with the active
ingredients according to the invention are as follows:
20 sulfur
dithiocarbamates and derivatives thereof, such as
ferric dimethyldithiocarbamate
zinc dimethyldithiocarbamate
zinc ethylenebisthiocarbamate
tetramethylthiuram disulfide
manganese-zinc ethylenediamine-bisdithiocarbamate
zinc-(N,N'-propylene-bisdithiocarbamate)
ammonia complex of zinc-(N,N'-ethylene)-bisdithiocarbamate
and
~L~L59~3
- 48 - O.Z. 0050/034525
N,N' polyethylene-bis-(thiocarbamoyl)-disulfide
ammonia complex o~ zinc-(N,M'-propylene-bisdithiocarbamate)
and
N,N'-polypropylene-bis-(thiocarbamoyl)-disulfide
nitro derivatives, such as
dinitro-(l-methylheptyl)-phenylcrotonate
2-sec-butyl-4,6-dinitrophenyl-3,5-d~methylacrylate
2-sec-butyl-4,6-dinitrophenylisopropylcarbonate
heterocycllc compounds, such as
N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalim~de
N-trichloromethylthio-tetrahydrophthalimide
2-heptadecyl-2-imidazoline acetate
2,4-dichloro-6-(o-chloroanilino)-s-triazine
0,0-diethylphthalimidophosphorothioate
5-amino-1-tbls-(dimethylamino)-phosphynyl]-3-phenyl-1,2,4-
-triazole
2,3-dicyano-1,4-dlthiaanthraquinone
2-thio-1,3-dithio-(4,5-b)-quinoxaline
methyl l-(butylcarbamoyl)-2-benzimidazole carbamate
4-(2-chlorophenylhydrazono)-3-methyl-5-isooxazolone
pyridine-2-thiol-1-oxide
8-hydroxyquinoline and its copper salt
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide
2-t~uryl-(2)3-benzimidazole
piperazine-1,4-diyl-bistl-(2,2,2-trichloroethyl)-formamide]
2-tthiazolyl-(4)]-benzimidazole
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
- 49 - O.Z. 0050/034525
and varlous fungicides, such as
dodecylguanidine acetate
3-[2-(3,5-dimethyl 2-oxycyclohexyl)-2-hydroxyethyl]-glutarimide
hexachlorobenzene
N-dichlorofluoromethylthio-N,N'-dimethyl-N-phenylsulfuric acid
diamide
2,5-dimethylfuran-3-carboxanilide
2-methylbenzoic acid anilide
2-iodobenzoic acid anilide
10 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
1-(4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,4-triazol-1-yl)-2-butanone
1-(4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,4-triazol-1-yl)-2-butanol
-(2-chlorophenyl)- -(4-chlorophenyl)-5-pyrimidine-methanol.
For the following experiment, the prior art active ingredient
l-t2-(2,4-dichlorophenyl)-2-(2-propenyloxy)-ethyl]-imidazole was
used as comparative agent D.
Action on wheat mildew
Leaves of pot-grown wheat seedlings of the "Jubilar" variety
are sprayed with aqueous emulsions consisting of 80% (by weight)
of active ingredient and 20% of emulsifier, and dusted, after the
sprayed-on layer has dried, with spores of wheat mildew (Erysiphe
graminis var. tritici). The plants are then placed in a greenhouse
at 20 to 22C and 75 to 80% relatlve humidity. The extent of
mildew spread is determined after 10 days. The results o~ this
experiment show that active ingredient nos. 35, 36, 62, 87, lOl,
108, 109 and 121 have a better fungicidal action than prior art
compound D.
