Note: Descriptions are shown in the official language in which they were submitted.
7 ~
o ~. r~50/356~7
1,3,5-Tri~inones and their use. ~or ccntrolli~g
undesirable plant gro~th
The present invention relates to 1~3,5~triazi-
nones, herbicides containing these compounds as -the
active ingredients1 and a method of controlling undesi-
rable plant growth using these active ingredients.
German Laid-Open Application DOS 2,246,109 has
disclosed the use of phenoxy~substituted N-phenyl-1,3,5-
triazinones~ such as l-[4-(2'-chloro-4'-trifluoromethyl-
phenoxy)-phenyl]-3-methyl-1,3,5-triazine 1-2,4,6-(lH,3H,-
5H)-trione, as drugs, especially as coccidiostatics.
We have found that 1,~,5-triazinones of the
formula
1 'J~ 2
O N3 0 (I)
R
zl
where R~ is ~ ~ Z3 where zl and z2
independently of one another are each hydrogen, halogen,
nitro, cyano or carboxyl, or alkyl, haloalkyl or alkoxy,
each of not more than 4 carbon atoms, Z3 is halogen,
nitro or cyano, or alkyl, haloalkyl, alkoxy, haloalkoxy,
alkylmercapto, haloalkylmercapto, alkylsulfinyl, halo-
alkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl, each
of not more than 4 ca-bon atoms, and Y is hydrcgen,
halogen, cyano or nitro~ and R2 is hydrogen or a
J5~
~ 2 ~ ~j.'. O()'(j/356~
saturated or unsatura-ted, s-traight-chaln or branched
aliphatic radical of not more than 20 carbon atoms, or
R is a saturated 7 straight chain or branched
allphatic radical of no-t more than 10 carbon atoms whi.ch
is substituted by halogen, cyano, hydroxyl or mercapto,
or by alkoxy or alkylmercapto 3 each of not more than
4 carbon atoms, or by phenylmercapto 7 or by alkylamino
or dlalkylamino, where each alkyl is of 1 to 4 carbon
atoms, or R2 is cycloalkyl of 3 to 7 carbon atoms l~hich
lG is ~nsubstituted or substituted by alkoxy o~ 1 to 4 car-
bon atoms, or R2 is phenyl which is unsubstituted or
substituted by halogen, or by alkyl or alkoxy, each of
1 to 4 carbon atoms, or by nitro or cyano, or 'Dy halo-
alkyl, haloalkoxy or haloalXylmercapto 9 each of 1 to 4
carbon atoms, or R~ is benzyl or halobenzyl, and R~ is
hydrogen, alkyl of n~ more than 4 carbon atoms or acyl
o~ not more than 7 carbcn atoms which is ~lsubstituted
or substituted by halogen, or is an alkali metal ion or
an ammonium ion, which may be alkylated, have very good
herbicidal proper-ties and are selective in crops.
In formula I, if Rl is
zl
Y ~ o ~ z3
zl and z2 independently of one another can each ~e, for
example, hydrogen, halogen, such as fluorine, chlorine,
bromine or iodine, nitro, c-~ano or carboxyl, or al~yl,
_ 3 _ O.Z. OO~(j/35~
haloalkyl or alkoxy 9 each of not more than 4 carbon atoms,
eg, meth-yl, ethyl, n-propyl, i-propyl, n-out;l, tert.-
butyl, trifluoromethyl, difluoromethyl, fluoromethyl,
trichloromethyl, dichloromethyl 9 chloromethyl, difluoro~
chloromethyl, l-chloroe~hyl, 2 chloroe~thyl, l-fluoroethyl,
2-fluoroethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl,
1,1,2,2-tetrafluoroethyl, 1,1,2 trifluoro-2-chloroethyl,
9 2 3 2,2-pentafluoroethyl, methoxy, ethox~J, n-propoxy,
i-propoxy or tert.-butoxy, and Z3 is ha].ogen, such as
0 fluorine, chlorine, bromine or iodine, or nitro or cyano,
or alkyl, haloalkyl, alkoxy, haloalkoxy, alkylmercapto,
haloalkylmercapto, alkylsulfinyl, haloalkylsulfinyl,
alkylsulfonyl or haloalkylsulfonyl, each of not more
than 4 carbon atoms, eg. methyl 9 ethyl 9 n-propyl) i-
propyl, n-butyl, -tert,-butyl, trifluoromethyl, di~luoro-
methyl, fluoromethyl, trichloromethyl, dichloromethyl,
chlorome-thyl, difluorochloromethyl, l-chloroethyl, 2~
chloroethyl, l~fluoroethyl, 2-fluoroethyl, 2,2,2-tri-
chloroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-te-tralluoro-
) ethyl, 1,1,2-trifluoro-2-chloroethyl, 1,1,2~2 t 2-penta-
fluoroethyl, methoxy, n-propoxy, i-propoxy~ tert,-
butoxy, trichlorometho~y, trifluoromethoxy, l-chloro-
ethoxy, 2-chloroethoxy, l-fluoroethoxy, 2-fluoroethox~J,
2,2,2~trichloroethoxy, 2,2,2-trifluoroetkoxy, 1,1,2,2-
tetrafluoroethoxy, 1,1,2,2,2-pentafluoroethoxy, methyl-
mercapto, ethylmercapto, trickloromethylmercapto, tri-
fluoromethylmercapto, methylsulfinyl, ethylsulfinyl,
methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl,
and Y can be, for example, halogen, such as fluorinet
_ 4 _ o.z GG~,o/356~7
chlorine, bromine or iodine, or h~drogen, c~Jano or nitro.
R2 in formula I is hydrogen, or is a saturated
or unsaturated, s-traight-chain or br~nched aliphatic
radical of not more than 20 carbon atoms, for example
alkyl of not more than 20 carbon atoms, preferably of
not more than 12 and especially of not more than 4 carbon
atoms, or alkenyl or alk~nyl of not more than 20 carbon
atoms, preferably of not more than 12 and especially o~
not more than 4 carbon atoms, eg. methyl, ethyl, n-propyl,
isopropyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl,
n-pentyl, tert -amyl, n-hexyl, pent-3-yl, l,2-dimethyl-
n-propyl, l,3-dimethyl-n-butyl, l-ethyl-2-methyl-n
propyl, l,2,2-trimethyl-n-propyl, l,2-dimethyl-4-hexyl,
allyl, methallyl, crotyl, 2-ethyl-hex-2-enyl, hex-5-enyl,
2-methyl-but-2-enyl, 2-methyl-but-3-enyl, but-l-en-~-yl,
2-methyl-but-l-en-4~yl, 2-methyl-but- 2-en-4-yl, 3
methyl-but-l-en-3-yl, propargyl, but~ n-3-yl or bu-t-2-
ynyl, or R is a saturated, straigh-t-chain or branched
aliphatic radical of not more than lO carbon atoms, pre-
2~) ferably of not more than 4 carbon atoms, which is sub-
stituted by halogen, cyano, hydroxyl, mercapto or alkoxy
o~ l to 4 carbon atoms, for example alkyl of not more
than lO carbon atoms, preferably of l to 4 carbcn atoms,
which is substituted by halogen, cyano, hydroxyl, mer-
capto or alkoxy of not more than 4 carbon atoms~ eg.
2-chloroethyl, 2-chloro-n-propyl, 3-chloro-n-propyl,
2-chloro-sec,-butyl, 2-chloro-isobutyl, 2-fluoro-sec.-
butyl, 2-fluoro-isobutyl, 2-fluoro-isopropyl, chloro-
tert -butyl, 2,2,2-trifluoroethyl, l-cyanomethyl,
~ ~ ~ s~j~7~
-- 5 ~
2-cyanomethy],, 2-hydroxyethyl, 3-hydroxy~n~propyl, 2-
mercapto-ethyl, 3-mercapto-n~propyl, 2-methoxye-thyl, 2-ethoxy-
ethyl, 3-methoxy-n-propyl, 2-methoxy-lsopropyl, 3-methoxy-n-
butyl, l-methoxy-sec.-butyl, methoxy-tert.-butyl, ethoxy-
tert.-butyl, 2~methoxy-n-butyl or 4-methoxy-n-bu-tyl, or R
is cycloalkyl of 3 to 7 carbon atoms which is unsubstltuted
or substituted by alkoxy of 1 to 4 carbon atoms, eg. cyclo
propyl, cyclopentyl, cyclohexyl or q-ethoxycyclohexyl.
R can also be a satura-ted, straight-chain or
branched aliphatic radical of not more than 10 carbon atoms
which is substituted by phenylmercapto, by alkylmercapto of
not more than 4 carbon atoms, or by alkyl- or dialkylamino,
where alkyl is of 1 to 4 carbon atoms, for example alkyl of
not more than 10 carbon atoms, preferably of 1 to 4 carbon
atoms, which is substituted by phenylmercapto or alkyl-
mercapto of 1 to 4 carbon atoms or by alkylamino or dialkyl-
amino, where each alkyl is of 1 to 4 carbon atoms, eg.
2-methylmercapto-ethyl, 2-ethylmercapto-ethyl, 3-methyl-
mercapto-n-propyl, 3-methylmercapto-n-butyl, l-methylmercapto-
2t) sec.-butyl, methylmercapto-tert.~butyl, 2-methylmercapto-n-
butyl, 2-methylaminoethyl, 2-ethylaminoethyl, 2-dimethyl-
aminoethyl, 2-diethylaminoethyl, 2-dimethylamino-n-propyl,
3-dimethylamino~n~propyl or 4-dimethylamino-n-butyl, or R2
ls phenyl which is unsubstituted or substituted by halogen,
or by alkyl or alkoxy of 1 to 4 carbon atoms, or by nitro or
cyano, or by haloalkyl, haloalkoxy or haloalkylmercapto of
1 to 4 carbon a-toms, or is benzyl or halobenzyl, eg. phenyl,
4-chlorophenyl, 3,4-dichlorophenyl, o-, m- or p tert.-
~ 0 Z. ~050/35~7bu-tylphenyl, o-, m- or p-metho.xyphen~l, o-, m- or p-
methylphenyl, 4-methory-3-chlorophen~l, 2-methyl-4-
chlorophenyl~ 4~nitrophenyl, 4-nitro-2-chlorophenyl,
o-, m- or p-cyanophenyl, o- or m trifluoromethylphenyl,
~-chloro-4-triIluorome thylphenyl 9 4-trifluoromethoxy-
phenyl, 4-trifluorometh~lmercaptophenyl, 3-trifluoro-
methylmercaptophenyl, benzyl, 2 9 6-dichlorobenzyl, 2-
chloro-6-fluorobenzyl, 2,6-diiluorobenzyl, or o~ or
p-chlorobenzyl.
R3 can be hydrogen, al~yl of no~ more than 4 car-
bon atoms, or acyl of not more than 7 carbon atoms, which
may be substituted by halogen, or an alkali metal ion or
an ammonium ion, l~hich may be alkylated~ eg~ methyl 9
ethyl, n-propyl, isopropyl, n-butyl, 2 butyl, formyl,
acetyl, chloroacetyl, benzoyl, sodium, potassium, ammo-
nium, methylammonium, dimethylammonium, trimethylammonium
or tetramethylammonium.
Preferred 1,3,5-triazinones are those compounds
of the formula I where Rl ls
Z~
Y ~ ~ ~ z3
where zl and z2 independently of one another are hydro-
gen, chlorine, bromine or cyano, Z3 ls chlorine, bromine,
methyl, trifluoromethoxy, trifluoromethylmercapto or
trifluoromethyl, preferably trifluoromethyl, ar.d ~ is
bromine or nitro, in particular nitro, and R2 is al~yl
of 1 to 4 carbon atoms, ~hich is ~substituted or sub-
stituted by halogen, cyano, alko~y or alkylmercapto, or
7~
- / - o.Z~ 0050/35~87
is cycloalkyl of 3 to '7 car'oon atoms, or is phenyl which
is substituted b~J haloalkyl of l to L, carbon atoms or
by halogen, or i~ halobenzyl, preferabl~J methyl, ethyl,
2-chloroethyl, 2-cyanoethyl, 2~methoxyethyl, 2-methyl-
mercaptoethyl, cyclohexyl, 3,4-dichlorophenyl, ~-tri-
fluoromethylphenyl or 4-chlorobenzyl, in par-ticular
methyl 9 2 chloroethyl, 2-methoxyethyl or 3,4-dichloro-
phenyl, &nd R~ is hydrogen, methyl or sodium.
~le compounds of the formula I where R3 is
hydrogen can be prepared, for example, by the following
process:
~ phenoxy-substituted urea of the formula
zl
O
~2 NHCNHR
where zl, z2, z3, y and R2 have the above rneanings, is
reacted with a substituted carbonyl isocyanate of the
form~la
o
R --C-~=C-0 (III)
where R4 is halogen, alXoxy or arylo~cy, in an inert
organic solvent, with or without addition of an acid
acceptcr, at from -20 to +180C 3 preferably from +20 to
+150C, at atmospheric or superatmospheric pressure,
l continuously or batchwise, to give a substituted 1,3J5-
triazinone of the formula
~.L~
o . z . o~ 5(j/356~7
,$ ' i P
where zl, z2~ z3, y and R2 have the above meanings.
If desired, this product can then be acylated or
al~ylated with an acyl halide of the ~ormula R3CoX, an
alkyl halide of the formula R3~ or a dîalkylsulfate of
the formula (R30)2So2, where R3 in each case has the
above meanings, with the exception of hydrogen, and X is
halogen 9 or converted into a salt of the formula I with
an alkali metal alcoholate, an alkali metal hydro~ide,
ammonium hydroxide or an alkylated ammonium hydroxide.
If N-3-(2'-chloro-4'-trifluoromethylpheno~3)-6-
nitro-phenyl-N'-methylurea and chlorocarbonylisocyanate
~re used as the starting substances and dimeth~31sulfate
.is used as the a~kylating agent, the course OL the reac-
tion can be represented by the following equa~ion:
o ~
HC~IHC~_ 1 C= ~12 0
~ - H C 1 ~ ,~
F C ~0 / ~ C~
3C4~'~' 0~1~)
C1 ~ H
C1
( C~30 ) 2SOG/
9 ~ O.Z. 0050/356~7
N2 0
F C- ~ 0 0 N o
3 ~ CH3
Cl
The reaction is carried out in organic sol~ents
which are inert under the partic~lar conditi.ons) ~or
example halohydrocarbons, in particular aromatic or
aliphatic chlorohydrocarbons, eg~ tetrachloroethylene,
1,1,2,2- or 19~ 2-tetrachloroethane, dichloropropane,
methylene chloride,dichlorobutane, chloro~orm9 chloro-
naphthalene, dichloronaphthalene 9 carbon tetrachloride,
1,1,1- or 1,1,2-trichloroethane, trichloroethylene,
pentachloroethane, o-, m- or p di~luorobenzene, 1,2-
I() dichloroethane, 1,l-dichloroethane, 1,2-cis-dichloro-
ethylene, chlorobenzene, fluorobenzene, bromobenzene,
iodobenzene, o-, m- or p-dichlorobenzene, o- 9 m- or p-
dibromo~.enzene, o- 9 m- or p-chlorotoluene or 1,2 9 4-
trichlorobenzene,ethers, eg. ethtJl propyl ether, me-thyl
tert.-butyl ether, n-butyl ethyl ether, di~n-butyl ether,
diisobutyl ether, diisoamyl ether, diisopropyl ether,
anisole, phenetole, cyclohexyl methyl ether, diethyl
ether, ethylene glycol dimeth~Jl ether, tetrah~Jdrofuran,
dioxane or ~,3'-dichlorodiethyl ether, nitrohydrocarbons,
eg~ nitromethane, nitroethane, nitrobenzene, o~, m- or
p-chloronitrobenzene and o-nitrotoluene, nitriles,
acetonitrile, butyronitrile, isobutyronitrile, benzo~
nitrile and m-chloroben70ni-trile, aliphatic or c~Jclo-
~ f~
- 10 - 0.~ )()50/350~
aliphatic hydrocarbons, eg~ heptarle, plnane, nonane,
o-, m- or p-c~Jmene, gasoline fractions ~ thin a boiling
point range of from 70 to 190C, cyclohexane, methyl-
cyclohexane, decalin, petroleum ether, hexane, naphtha,
2 9 2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-
trlmethylpentane and octane, esters, eg. e-thyl acetate,
ethyl acetoacetate and isobutyl ace-tate, amides, egq
formamide, methylformamide and dime-thylformamlde, and
ketones, egu acetone and methyl ethyl ketone, and app~op_
riat~ mixtures. The solvent is advantageously used in
an amount of from 100 to 2,000% by weight, preferably
from 200 to 700% by ~eight, based on the starting
substances~
l~e hydrochloric acid formed during the reaction
escapes as a gas, or is bonded by acid acceptors. ~ny
o~ the conventional acid acoeptors can be used, pre-
ferably tertiary amines, alkaline earth metal compounds 7
al~monium compounds and alkali metal compounds or appro-
priate miYtures9 Zinc compounds can also be used.
'0 Examples o~ suitab].e basic compounds are potassium
hydroxide, sodium carbonate~ lithium hydroxide 9 lithium
carbonate, sodium bicarbonate 9 potassium bicarbonate,
calcium hydroxide, calcium oxide, barium oxide~ magnesium
hydroxide 9 magnesium oxide, barium hydroxide, calcium
carbonat~, magnesium carbonate, magnesium bicarbonate 9
magnesium acetate 9 zinc hydroxide 9 zinc oxide, zinc
carbonate, zinc bicarbonate, zinc acetate, sodium formate~
sodium acetate 7 trimethylamine, triethylamine t trlpropyl-
amine, triisopropylamine, tributylamine, -triisobutylamine 7
rj~f~r~
~ .Z. ()050/35~7
tri-sec butylamine, tri-~ert -bu~tylamine, tribenzylamine,
tricyclohexylamine~ ~riamylamine~ diisopropylethylamine,
trihexylamine, N,M~dimethyl~niline, N,N-diethylaniline,
N,N dipropyltoluidine, N,N-dimethyl-p-aminopyridine,
N-methylpyrrolidone, N-ethylpyrrolidone, N~methylpiperi-
dine, N-ethylpiperidine 7 N-methyl-pyrrolidine, N-ethyl-
pyrrolidine, N~methylimidazole, N-ethylirnidazoIe, N-
methylpyrrole, N-ethylpyrrole, N-methylmorpholine, N-
ethylmorpholine, N-methylhexamethyleneimine, N-ethyl-
hexamethyleneimine, pyridine, quinoline, a-picoline,
~-picoline 9 ~-picoline, isoquinoline~ pyrimidine,
acridine, N,N,N',N'-tetramethyleth~Jlenediamine, N,N,N',-
N'-tetraethylethylenediamine, quinoxaline, quinazoline,
N-propyldiisopropylamine, N,N-dimethylcyclohex~lamine,
2,6-lutidine, 2,4-lutidine, trifurfurylamine and tri-
ethylenediamine.
The starting substances are reacted in, for e~-
ample, approcimately the stoichiometric ratio, iec
starting substance III can be employed in, for example 9
an eccess of not more than 20 mole%, based on II.
The process for the preparation of the compounds
of the formula I is advantageously carried out by taking
the starting substance II, if appropriate in one of ~he
above diluents, and then adding t~e starting substance
III and, where appropriate, an acid acceptor, at the
s~me time or successively. However, it is also pos-
sible to take the starting substance III in a diluent
and then to add the starting substance II and an acid
acceptor by -two separate lines, at the same tlme or in
12 - ~J Z ~,050/356?,7
~ither order.
In many cases, the reaction has ende~-once
the components ha~re been brought ~o~ether, other~ise
~he mixture is sti~red for a ~ur~her period o~ from 10
minutes to 10 hours at from ~20 to 180C, pre~f~rably
from 20 to 150C and in particular from 40 tc lOO~C,
until the reac-tlon has ended
If an inert gas is used to remove the hydrogen
halide, stirring is adv~ltageously continued for from
O~2 to 10 hours at from 40 to 100C.
~ he end product I is isolated from the reaction
mixture in a conventional manner, for example a~ter
distilling off solvents or excess starting substance III
or directly by filtration with suction~ In this case,
the residue which remains is washed with water or dilute
alkali, to remove acid impurities, and dried. If
water-immiscible diluents are used, the reaction mi~ture
can also be extracted directly with water or with dilute
alkali and the extract then dried and concentrated.
~) However, it is also possible to dissolve the residue in
a water-immiscible solvent and to wash the solution as
described. m e desired end products are thereby
obtained in a pure form, and if necessary they can be
purified by recrysta lization, chromatography or distil-
lation.
The compounds of the formula I where R' is alkyl,
acyl, an alkali metal ion or an ammonium ion which may
be alkylated can be prepared from the correspo~ding com-
pounds of the ~ormula I where R3 is hydrogen , in a
5~
-- 13 ~ O Z. 0~50/35687
conventional manner Alkylation is ef~ected by means
of alkylating agents, such as alkyl halides (eg~ methyl
bromide or ethyl iodide), dialXylsulfates (eg. dimethyl-
sulfate or diethylsulfate) or OXOIliUm salts (eg tri-
methyloxoniumtetrafluoborate), in the presence or absence
of an inert orga~ic solvent and i^n the presence or
absence of an acid acceptor, at from -20C -to 100C,
preferably from O to 100C, under atmospheric or super-
atmospheric pressure, continuously or batchwise.
Acylation is effected by means of acyl halides (eg.
acetyl chloride or benzyl chloride), in the presence orabsence of an inert organic solvent and in the presence
or absence of an acid acceptor, at from -20C to 150C,
pre~erably from 20 to 120C, under atmospheric or super-
atmospheric pressure, continuously or batchwise
To prepare a salt, a compound of the formula I
where R3 is hydrogen is advantageously dissolved in an
or~anic solvent, eg. methanol, approximately the stoi-
chiometric amount of alkali metal alcoholate, eg. sodium
.~0 methylate, alkali metal hydroxide, eg. sodium hydroxide,
ammonium hydroxide or alkylated ammonium hydroxide is
added,and the mi~ture is concentrated to dryness
m e starting compounds can be prepared in a con-
ventional ma~ner ~hus, the phenoxy-substituted ureas
of the formula II are prepared by, for example, the pro-
cedure described in German Laid-O~en Application DOS
2,942,3~0. The co~pounds of the formula III can be
prepared by ~ethods disclosed in tne literatuLre (AnOe~.
Chem. 89 (1977), 789).
~ 14 ~ (~ z 0050/35687
The Examples which follow illus-tra-te the pre-
paration of the compounds oi the formula I by the 2rocess
described. Parts by weight bear the same relation to
parts by volume as that of the kilogram to the liter.
EXAMPI~:E 1
A solution of 6 t 4 parts by weight of M~chloro-
carbonyl isocyanate in 5 parts by volume of ab~o'.ute
toluene is added to a suspension of~ 19 4 5 parts by weight
of N-3-(2'~chloro-4'-trifluoromethylphenox~J)-6-nitro-
phenyl~N'-methylurea in 25 parts by volume of absolute
toluene. The reaction mixture is heated, and is then
- stirred under reflux for two hours. After cooling,
n-pentane is added ~nd the precipitate formed is filtered
off with suctionO 19 parts by weight (83C~o of theory)
o~ 3'~(2"-chloro-4"-trifluoromethylphenoxy)-6'-nitro-
phenyl]-3-methyl-1,3,5-triazine-2,4,6-(lH~3H,5H)-trione
(compound No. 1) of melting point 208-211C &~e
obtained.
EXAMPLE 2
A solution of 8 parts by weight of compound No. 1
in 100 parts by volume cf acetone is stirred under reflux
with 2.4 parts by weight of potassium carbonate and
2.2 parts by weight of dimethylsulfate for two hours.
m e reaction mixt~re is filtered, the filtrate is evapo-
rated under reduced pressure~ &nd the residue is recrys-
tallized from diisopropyl ether. 8 parts by weiOht
(970,6 of theory) of 1-[3'-(2'7-chloro-4"-trifluoromethyl-
phenoxy)-o'-nitrophenyl]-3,5-dimethyl~1,3,5-triazine-
2,4,6-(lH,3H75H)-trione (compound No. 2) of melting
- 15 - o.z. 0050/356~7
point 200-205 C are obtained.
~ EX~PLE 3
5 parts by weight of compound No. 1 are suspended
in 50 par-ts by volume of absolute methanol, and 1.96 parts
by weight of 30~0 strength methanolic sodium methylate
solu-tion ar~ added. The mi~ture is stirred at room
temperature for 30 mlnutes and is evaporated under
reduced pressure~ 5 parts by weight (99% o~ theory)
of the sodium sal-t o~ 3'~(2'7-chloro-4"-trifllloromethyl-
phenoxy)-6'-nitrophenyl] 3-methyl-1,3,5-triazine-2,4~6-
lo (lH,3H,5H)-trione (compound No, 3) of melting point
220-225C are obtained.
The compounds listed in the Ta~l~ below are
prepared in a manner similar to that in the above
Examples.
&~
- 16 - O.Z. 0050/35~87
,~
~I
C)
U~
Ln
~a o~
~- b` O C~ O
3~
u~ '3
~ ~ c.~ z c~ o-c~ o c~ z ~ c~ z :c c~
5:
C~
~ ~ ~ o ^
~l 5: 0 ~
~0
b
o
.~
~ : : : : : = - _
I
c~- ~ ~ a~
O
O O
I a~
æ
7~-~
- 1 7 - O . Z . 0050/3 S 6 ~ 7
.~
~:
o o
.
o~ ~
U~ ~1 0
n ~ u~ O
o~ o
\ ,C h ~ I
O O
U~ ~ O CO
o~: ~1 a~
~ ~ o
~1 _ ~
O O
a~
5~ 3
1 0 ~
Z ,~ C_) Z ~ C,~ Z 5~ t.) Z ~ ~ Z ~C t.) Z ~ ~.) Z
t~
11 ~ O U~ O
~q ~ ~ ~`1
I O C~
t~
~0
~U
.,1
~ ~ ~,1
~ 0~
h
O O
I ~
O ~ ~ ~ ~ u~ O ~ ~ ~ ~ ~n ~D ~ CO
O ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~1 ~ ~ ~ r~
z
~ 18 - O.Z. 0050/35687
-
h
C~
a~
n
O
~`3 ~ G ~ ~ O O ~4 (`
~1 ~ ~ ~ ~`I ~
o b b b o I
o~ ~ o ~ o o
a) ~ ~ ~o
~ .,,
aJ
~ ~ ~ o
5~ 3
7 ~ ~ r~
~ ~ rd ~ ~ 5~ 0 ~ ,a ~ ,a
LO ~ ; C) Z $ ~ Z ~ ~ Z ~ C~ Z ~q O Z ~ æ
Lr)
~ X
~ ~ O
C~ ~ ~ ~ 5: ~
U~ ~ o o U
~ ~ o o ~ i
C~
o U ~ o o
~ ~ C ~ ) ~('`1 N
c~ o u
x
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h
O O
SS
t.) I'
I
t5~ 0 ~ t`~ ~ ~ Q
z
- 19 - O.Z. 0050/~56~7
~ )
r~ Q~
~1 O
~a o~ ,.~
r~
o ~ o
~ r~ I r,~
C) ~ ~ ~ o r~
o ~ I o I ~
_ ~ ~ O ~ U~ ~ Ln
r~ o ~ ~
r-l r-l r-l
O
~ ~ 11
:~ 3~ r
~- ~ r~
1 0 ~:;
~C ~.) Z~:a rJ ~ C~ Z 51 r ) ~ C ) Z ~C C~ Z 51 C~
j_ u~
r~ r~
tC ~`I t~ ~'I
c~
~; C) ~ u~ V r~ a
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- 25 - O.Z. 0050/35687
The compounds of -the formula I, or herbicidal agents con-
taining them, may be applied for instance in the form of directly
sprayable solutions, powders, suspensions (inclucliny high-percen-
tage aqueous, oily or other suspensions), dispersions, emulslons,
oil dispersions, pastes, dusts, broadcasting agents, or granules
by spraying, atomizing, dusting, broadcasting or watering. The
forms of applicatlon depend enti.rely on the purpose for which the
agents are being used, but they must ensure as fine a distribution
of the active ingredients according to the invention as possible.
For the pre2aration of solutions, emulsions, pastes and oil
dispersions to be sprayed direct, mineral oil fractions of medium
to high boiling point, such as kerosene or diesel oil, further
coal tar oils, and oils of vegetable or animal origin, aliphatic,
cyclic and aromatic hydrocarbons such as benzene, toluene, xylene,
paraffin, tetrahydronaphthalene, alkylated naphthalenes and their
derivatives such as methanol, ethanol, propanol, butanol, chloro-
form, carbon tetrachloride, cyclohexanol, cyclohexanone, chloro-
benzene, i.sophorone, etc~, and strongly polar solvents such as
dimethylformamide, dimethyl sulfoxi.de, N-methylpyrrolidone, water,
2~ ~tc. are suitable.
Aqueous formulations may be prepared from emulsion concen-
trates, 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 homoge-
nized in water by means of wetting or dispersing agents, adherents
or emulsifiers. Concentrates which are suitable for dilution with
-- 26 - O.Z. 0050/35687
water may be prepared from active ingredient, wettiny agent, ad-
herent, emulsifying or dlspersing agent and possibly solvent or
oil.
Examples of surfactants are: alkali metal, alkaline earth
metal and alnmonium salts of ligninsulfonic acid, naphthalenesul-
fonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl
sul~ates, and alkyl sulfonates, alkali metal and alkaline earth
metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sul-
fate, fatty alcohol sulfates, alkali metal and alkaline earth
metal salts of fatty acids, salts of sulfated hexadecanols, hepta-
decanols, and octadecanols, salts of sulfated fatty alcohol glycol
ethers, condensation products of sulfonated naphthalene and
naphthalene deri~atives with formaldehyde, condensation products
of naphthalene or naphthalenesulfonic acids with phenol and form-
aldehyde, polyoxyethylene octylphenol ethers, ethoxylated isocctyl-
phenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkyl-
phenol polyglycol ethers, tributylphenyl polyglycol ethers, alkyl-
aryl polyether alcohols, isotridecyl alcohol, fatty alcohol
ethylene oxide condensates, ethoxylated castor oil, polyo~y
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
mixing or grinding the active ingredients with a solid carrier.
Gxanules, e.g., coated, impregnated or homogeneous granules,
may be prepared ~y bonding the active ingredients to solid car-
riers. Examples of solid carriers are mineral earths such as
- ~7 ~ O.Z. 0050/35687
silicic acid, sillca gels, silicates, talc, kaolin, ~ttaclay,
limestone, lime, chalk, bole, loess, clay, dclomite, diatomaceous
earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground
plastics, fertili2ers such as ammonium sulfate, arnmonium
phosphate, ammonium nitrate, and ureas, and vegetable products
such as grain flours, bark meal, wood meal, and nutshell meal,
cellulosic powders, etc.
The formulations contain from 0.1 to 95, and preferably 0.5
to 90~ % by weight of active ingredient.
~xamples of formulations are given below:
I. 90 parts by weight of compound no. 1 is mixed with 10 parts
by weight of N~methyl-alpha-pyrrolidone. A mixture is obtained
which is suitable for application in the form of very fine drops.
II. 20 parts by weight of compound no. 38 is dissolved in a
mixture consisting of 80 parts by weight of xylene, 10 parts by
weight of the adduc-t of 8 to 10 moles of ethylene oxide and 1 mole
o~ oleic acid-N-ntonoethanolamidel 5 parts by weight of the calcium
salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the
aclduct of 40 moles of ethylene oxide and 1 mole of castor oil. By
~ pou~lng the solution into 100,000 parts by weight of water and
urliformly distributing it therein, an aqueous dispersion is
obtained containing 0.02% by weight of the active ingredient.
III. 20 parts by weight of compound no. 3 is dissolved in a mix-
ture consisting of 40 parts by weight of cyclohexanone, 30 parts
by weight of isobutanol, 20 parts by weight of the adduct of
7 moles of ethylene oxide and 1 mole of isooctylphenol, and
10 parts by weight of the adduct of 40 moles of ethylene oxide and
r j t~
- 28 -- o. æ . 0050/35687
1 mole of castor oil~ By pouring the solution into lO0,000 parts
by weight of water and finely dis~rlhuting it -therein, an aqueous
dispersion is obtained containing 0.02~ by weight of the active
ingredient.
IVo 20 parts by weight of compound noO 3 is dissolved in a mix-
ture consisting of 25 parts by weight of cyc]ohexanol, 65 parts by
weight of a mineral oil fraction havlng a boiling point between
210 and 280C, and 10 parts by weight of the adduct of 40 moles
of e-thylene oxide and l mole of castor oil~ By pouring the
solution into 100,000 parts by weight of water and uniformly
distributing it therein, an aqueous dispersion is obtained contain-
ing 0.02% by weight of the active ingredient.
V. 80 parts by weight of compound no. 37 is well mixed with
3 parts by weight of the sodium salt of diisobutylnaphthalene-
-alpha-sulfonic acid, lO parts by weight of the sodium salt of a
lignin-sulfonic acid obtained from a sulfite waste liquor, and
7 parts by welght of powdered silica gel, and triturated in a
hammer mill.
VI. 3 parts by weight of compound no. 36 is intimately mi~ed with
~l7 parts by weight of particulate kaolin. A dust is obtained con-
taining 3~ by weight of the active ingredient.
VII. 30 parts by weight of compound no. l 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.
35 ~ ~ ~
- 29 - O.Z. 0050/35687
VIII. 20 parts of compound no. 1~6 is intima~ely mixed wlth
2 parts of the calcium salt of dodecylbenzenesulfonic acidt
8 parts of a fatty alcohol polyqlycol ether, 2 parts of the sodium
salt of a phenolsulfonic acid-urea-formaldehyde condensate and
68 parts of a parafflnic ~ineral oil. A stable oily dispersion is
obtained.
The herblcidal agents may be applied pre- or postemergence.
If certain crop plants tolerate the active ingredients less well,
application techniques may be used in wh:ich the herbicidal agents
are spray~d from suitable equipment in 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 growiny beneath
the crop plants (post-directed, lay-by treatment).
The amount of active ingredient applied depends on the time
of the year and the growth stage of the plants, and varies from
0.025 to 10 kg/ha and more, but is preferably from 0.1 to 4 kg/ha.
The higher application rates are particularly suitable for total
elimination of vegetation.
The herbicidal action of compounds of the formula I or
herbicidal agents containiny them is demonstrated in greenhouse
experiments.
The vessels employed were plastic flowerpots having a volume
of 300 cm3, and which were filled with a sandy loam containing
about 1.5% humus. The seeds of the test plants were sown shallow,
and separately, according to species. For the preemergence treat-
ment, the active ingredients were applied to the surface of the
soil immediately after the seeds had been sown. The compounds were
g5~
- 30 - O.Z. ~050/356~7
emulsified or suspended in water as vehicle, ,~nd spra~ed through
finely distributing nozzles. After the agents had been applied,
the vessels were lightly sprinkler-irrigated to induce germination
and growth and to activate the chemical ayents~ Txansparent
plastic 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.
For the postemergence treatment~ the plants were Eirst grown
in the vessels to a height of from 3 to lS cm, depending on growth
form, before ~eing treated. The rice plants used for the postemer-
gence treatment were grown in a peat-enriched substrate. Peat was
also added to the soybeans to ensure better growth than in the
abovementioned soil. For this treatment, either plants which had
been sown directly in the pots and grown there were selected~ or
plants which had been grown separately as seedlings and trans-
planted to the experiment vessels a few days before treatment.
The pots were set up in the greenhouse - species from warmer
areas at from 20 to 35C, and species from moderate climates at
L5 to 25C. The experiments were run for from 3 to 4 weeks. During
this period, the plants were tended and their reactions to the
various treatments assessed. The scale used for assessment was 0
to 100, 0 denoting no damage or normal emerc~ence, and 100 denoting
nonemergence or complete destruction of at least the visible plant
parts.
The test plants employed were Abutilon theophrasti,
Amaranthus spp., Arachis hypogaea, Chenopodium album, Datura
~f,~
O.Z. 0050/35687
stra.monium, Echinochloa crus~galli, Galeopsis ~etrahit, Glycine
max., Oryza sativa, Sesbania exaltata, Sida spinosa, Sinapis alba,
Solanum nigrum, Triticum aestivum, and Zea mays.
The prior art compound usecl for comparison purposes was
1-[4'~(2"-chloro-4"-trlfluoromethyl-phenoxy)-phenyl]-3-methyl-
-1,3,-5-triazine-2,4~6-trione (German Laid Open Appllcation
DE-OS 22 46 109).
The results of the greenhouse exper:iments reveal that for
instance compounds nos. 1, 36 and 37, applied preemergence at a
rate of, for example, 3.0 kg/ha, have a good herbicidal actlon.
On investigations into selective herbicidal properties on
postemergence application, compound no. 4, at 0.5 kg/ha, proves to
have a better action on the broadleaved weed Chenopodium than the
comparative agent, without damaging soybean and Indian corn
plants.
For instance compounds nos. 1, 3, 36, 37, 38, 44, 45, 69, 90,
93, 146 and 148, applied postemergence at rates of 0.06, 0.125,
0.25 and 0.5 kg/ha, combat a number of unwanted broadleaved
plants, depending on the active ingredient, in crops such as rice,
O wheat and groundnuts.
In view of the good tolerance of the active ingredients and
the many application methods possible, the compounds according to
the invention may be used in a large number of crop plants for
removing unwanted plant growth.
The following crop plants may be mentioned by way of example:
DI~
32 - O.Z. 0050/35687
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 vulgaris spp. rapa fodder beets
Beta vulgaris spp. esculenta table beets, red beets
Brassica napus var~ napus rape
Brassica napus var. napobrassica
Brassica napus var. rapa turnips
Brassica rapa var. silvestris
Camellia sinensis tea plants
Carthamus tinctorius safflower
Carya illinoinensls pecan trees
Ci.trus limon lemons
Citrus maxima grapefruits
Citrus reticulata mandarins
Citrus slnensis orange trees
Coffea arabica (Coffea canephora,
CofEea 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
~ ¢~'~t~
~ 33 - O.Z. 0050/35~87
Botanical_name _ _ Common name
Glycine max soybeans
Gossypium hirsutum
(Gossypium arboreum cotton
~ossypium herbaceum
Gossypium vitifolium)
~elianthus annuus sunflowers
Helianthus tuberosus
Hevea brasiliensis ruhber plants
Hordeum vulgare barley
~umulus lupulus hops
Ipomoea batatas sweet potatoes
Juglans regia walnut trees
Lactuca sativa lettuce
Lens culinaris lentils
Linum usitatissimum flax
Lycopexsicon lycopersicum tomatoes
Malus spp. apple trees
Manihot esculenta cassava
~le~icago sativa alfalfa (lucerne)
Mentha pi.perita peppermint
Musa spp. banana plants
Nlcothiana tabacum tobacco
(N. rustica)
Olea europaea olive trees
Oryza sativa rice
Panicum miliaceum
Phaseolus lunatus limabeans
Phaseolus mungo munybeans
Phaseolus vulgaris snapbeans, green beans,
dry beans
Pennisetum glaucum
r3~
- 34 - O.Z. 0050/356~7
Botanical name Common narne
Petroselinum crispum parsley
spp. tuberosum
Picea abies ~orway spruce
Abies alba fir trees
Pinus spp. pine trees
Pisum sativum English peas
Prunus avium cherry trees
Prunus domestica plum trees
Prunus dulcis almond trees
Prunus persica peach trees
Pyrus cornmunis pear trees
Ribes sylvestre redcurrants
Ribes uva-crispa gooseberries
Rlcinus communis castor-oil plants
Saccharum oEficinarum sugar cane
Secale cereale rye
Sesamllm indicum sesame
Solanum tuberosum Irish potatoes
Sorghum bicolor (s. vulgare) sorghum
~0
Sorghum dochna
Spinacia oleracea spinach
Theobroma cacao cacao plants
Trifolium 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
~ 35 - O.Z. 00~0/35687
To increase the spec-trum of action and to achieve synergistic
effects, the novel compounds according to the invention may be
mixed and applied together with numerous representatives of other
herbicidal or growth-regulating actlve inyredient groups~ Examples
of suitable mixture components are diAzlnes, 4H-3,1-benzoxazine
derivatives, benzothiadiazinones, 2,6-dinitroanilines, N~phenyl-
carbamates, thiolcarbamates, halocarboxylic acids, triazines,
amides, ureas, diphenyl ethers, triazinones, uxacils, benzofuran
derivatives, cyclohexane-1,3-dione derivatives, etc.
It may also be useful to apply the agents according to the
invention, either alone or in combination with other herbicides,
in admixture with other crop protection agents, e.g., agents for
combating pests or phytopathogenic fungi or bacteria. The com-
pounds may also be mixed with solutions of mineral salts used to
remedy n~ltritional or trace element deficiencies. Non-phytotoxic
oils and oil concentrates may also be added.
)o
