HERBICIDES

HERBICIDES

Abrégé anglais

Abstract of the disclosure:
Compounds of the formula
<IMG> I
have a good herbicidal action in pre-emergence and post-emer-
gence application against important weed grasses and are well
tolerated by dicotyledoneous crop plants and various cereals
so that the compounds are suitable for the selective control
of weed grasses in agricultural crops.

Revendications

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A compound of the formula
<IMG> I
in which
R1 is halogen, CF3 or C1-C4 alkyl,
Z is -CN, -CS-NH2, CO-R2 or -CH2-O-R3,
R2 is hydroxy, -0-cat; C1-C12-alkoxy (optionally substituted by OH, halogen,
CF3, C1-C6 alkoxy, C1-C4alkylthio, phenyl, phenoxy or halophenoxy), a
radical of one of the formulae
<IMG> <IMG> <IMG>
<IMG> , <IMG>
<IMG>,
in which <IMG> stands for the pyrrolidinyl, piperidinyl, morpholinyl or
N-methyl-piperazinyl radical; C5-C6 cycloalkoxy (optionally substituted by
C1-C4 alkyl, and/or halogen), C3-C4 alkenyloxy; cyclohexenyloxy; C3-C4
alkinyloxy (optionally substituted in l-position by C1-C4 alkyl and/or
phenyl), phenoxy (optionally substituted by halogen, NO2 and/or C1-C4 alkyl),
18

C1-C6 alkylthio, allylthio, phenylthio, halophenylthio, amino, C1-C4
alkylamino, hydroxyethylamino, di-C1-C4 alkylamino, pyrrolidino, piperidino,
morpholino; anilino (optionally substituted by halogen, CF3 and/or C1-C4
alkyl); or hydrazino,
R3 is hydrogen, C1-C4 alkyl, C1-C4 alkylcarbonyl, halo-C1-C4 alkylcarbonyl,
benzoyl (optionally substituted by halogen, NO2 and/or C1-C4 alkyl), C1-C4
alkylcarbamoyl, di-cl-c4alkylcarbamoyl, phenylcarbamoyl (optionally sub-
stituted by halogen and/or C1-C3alkyl), C1-C4alkylsulfonyl, phenylsulfonyl,
-SO3H or -SO3cat,
cat is the cation equivalent of an inorganic or organic base,
n is an integer of from 1 to 3 and
m is an integer of from 1 to 6,
on the proviso that when R1 is 4-CF3 n being 1, or R1 is 4-CF3 and 2-halogen,
n being 2, then R2 is not hydroxy, an -0-cation group, lower alkoxy, C1-C4
alkylthio, amino, C1-C4 alkylamino or di-C1-C4 alkylamino.
2. A compound as claimed in claim 1, in which (R1)n represents 4-chloro,
4-trifluoromethyl or 2,4-dichloro and Z stands for a radical of the formula
-CH2-0-R3 in which R3 has the indicated meaning.
3. A compound as claimed in claim 1, in which (R1)n represents 4-chloro
or 2,4-dichloro and Z stands for a radical of the formula -CO-R2 in which R2
has the indicated meaning.
4. A compound as claimed in claim 3, in which (R1)n and Z have the
indicated meaning and R2 represents hydroxy, -Ocat, C1-C12alkoxy optionally
substituted by -OH, halogen, -CF3, C1-C6alkoxy, C1-C4alkylthio, phenyl,
phenoxy, or halophenoxy; radicals of the formula
19

<IMG>
or -(OC2H4)2-3 - OCmH2m-l ;
C5-C6cycloalkoxy optionally substituted by Cl-C4 alkyl and/or halogen;
C3-C4alkenyloxy, cyclohexenyloxy, C3-C4alkinyloxy optionally substituted
in 1-position by C1-C4alkyl and/or phenyl; phenoxy optionally substituted
by halogen, NO2 and/or C1-C4 alkyl; C1-C6alkylthio, allylthio, phenylthio
halophenylthio and m stands for an integer from 1 to 6.
5. A compound as claimed in claim 1, having the formula
<IMG>
6. A compound as claimed in claim 1, having the formula
<IMG>
7. A compound as claimed in claim 1, having the formula
<IMG>
8. A compound as claimed in claim 1, having the formula

<IMG>
9. A compound as claimed in claim 1, having the formula
<IMG>
10. A process for preparing a compound of formula I as claimed in claim
1, which comprises
a) reacting a compound of formula
<IMG> II
with a compound of formula
<IMG>
III
in which Z .is a halogen atom or the mesylate or tosylate radical, in the
presence of a base, or
b) reacting a compound of formula II with .gamma.-valerolaction of
formula
<IMG> (IV)
in the presence of a base,
and optionally transforming the compound of formula I into another compound
21

of formula I by saponification, esterification, salt formation, transesteri-
fication, amidation, dehydration, hydration, reduction, or oxidation.
11. Method for controlling the growth of undesired weed grasses which
comprises treating the infested area with an effective amount of a compound
as claimed in claim 1.
22

Description

~ 8168 ~OE 76/F ?
This inv~ntion relates to compounds of the formula
CH3
in which
R1 is halogen, CF3 or C1-C4 alkyl,
Z is -CN, -CS-NH2,~CO-R2 or -CH2-O-R3,
R2 is hydroxy, -O-cat; C1-C~2alkoxy (optionally substituted by
OH, halogen, CF3, C1-C6alkoxy, C1~C4alkylthio, phenyl, phencx~.
or halophenoxy), a radical of one of the formulae
~o7 ~ , -oc~2~
2 ~1)2-~ CmH2m~ oc2il4-N
(c~-c4)alk
2 4 __
in which -N A stands for the pyrrolidinyl, piperidinyl., mor-
pholinyl~or N-methyl-piperazi.nyl radical; C5-C6cycloalkoxy (op-
tionally substituted by C1-C4al]cyl, and/or haloyen), C3-C4alke-
~ r,yloxy; cyclohex~-nyloxy; C3-C~alkin~loxY.. (Qptionall;v sl~bstitut~d in 1-posi.ti~ by
.. ~ C1-C4alkyl and/or phenyl), phenoxy ~cptionally substituted by
halogen, NO2 and/or C1-C4alkyl), C1-C6alkylth.io, allylthio, pher
thi.o, halophenylthio, amino, C1-C4alkylamino, hydroxyethylamino,
di-C1-C4al~sylamino, pyrrolidino, piperidino, morpholino; anilir.o
(optionally substituted by halogen, C~3 and/or C1-C4alkyl~; or
hydrazino,
R3 is hydrogen, C1-C4alkyl~ C1-C4alkylcarbonyl, ha~o~C1-C4alkyl-
' carhonyl, benzoyl (optlonal1y substituted hy halogen, NO2 an~ o^
.
' ' ,
-
'' . ~ ,

16¢~3
Cl-C4alkyl), Cl-C4alkylcarbamoyl, di-Cl-C4alkylcarbamoyl, phenylcarbamoyl
~optionally substituted by halogen and/or Cl-C3alkyl), Cl-C4alkylsulfonyl,
phenylsulfonyl, -S03H or -S03cat,
cat is the cation equivalent of an inorganic or organic base,
n is an integer of from 1 to 3 and
m is an integer of from 1 to 6,
on the proviso that when Rl is 4-CF3 n being 1~ or Rl is 4-CF3 and 2-halogen,
n being 2, then R2 is not hydroxy, an -O-cation group, lower alkoxy, Cl-C4
alkylthio, amino, Cl-C4 alkylamino or di-Cl-C4 alkylamino.
"cat" preferably is the cation equivalent of an inorganic base
such as Na , K , 1/2 Ca and 1/2 Mg , or NH4 and cations of organic amines
such as the various aliphatic mono-, di- and tri-alkylamines, the corresponding
; triethanolamines, aniline, methylaniline, benzylamine and diphenylamine.
Preferred halogens are chlorine and bromine.
If the radicals R2 or R3 contain substituted phenyl groups these may
; contain up to three and preferably one substituent; in the case of alkyl groups
as substituen*s methyl or ethyl are preferred.
Preferred compounds of formula I are those in which (Rl)n represents
4-chloro, 4-trifluoromethyl or 2,4-dichloro and Z is a radical of the formula
-CH2-0-R3 in which R3 has the indicated meaning.
Further preferred compounds of formula I are those in which ~Rl)n
represents 4-chloro or 2,4-dichloro and Z s~ands for a radical of the formula
-CO-R2 in which R2 has the indicated meaning.
Especially preferred compounds are those in which (Rl)n is 4-chloro
or 2,4-dichloro, Z a radical of the formula -CO-R2 and R2 is hydroxy, -Ocat,
Cl-C12alkoxy ~optionally substituted by -OH, halogen, -CF3, Cl-C6alkoxy,
Cl-C4 alkylthio, phenyl,
- 3 -
''~' i~
.
,

110 8~6 8 H0~ 76/E1 ~00
phenoxy, or halophenoxy), radicals of the formula
-OCH2 ~ , -OCH2 ~ , -OCH2 ~ ~ -
or~ -(oc2H4)2_3 - C~.H2m-1;
C5-C6cycloalkoxy (optionally substituted by C1-C4alkyl and/or
halogen), C3-C4alkenyloxy, cyclohexenyloxy, C3-C~alkinyloxy
(optionally substituted in 1-position by C1-C~alkyl and/or
phenyl), phenoxy (optionally substituted by halogen, N02 and/or
C1-C4alkyl), C1-C6alkylthio, allyl.thio, phenylthio or halophenyl-
thio and m i.s an integer from 1 to 6.
The compounds of formula I can be prepared by a variety of
methods.
a) The compounds I are obtained, ~or example, by reacting com
~. pounds of the formula III with compounds of the formula II,
.~ according to the followin~ reactjon scheme
(R)n ~ ~~ ~ C CH2CH2Z ~-~
II ~II
(R)n ~ ~ ~ -O-C~-CH2c~i2ZiHy
-
. I
In th~ a~oresaid ~ormulae Y is halogen, preferably bromine
,- ,1
or chlorine, or the mesylate or the tosyl.ate radical. The
.. reaction is pre~erably carried out under basic conditions at a
temperature in the ran~e of from 20 C to the ~oiling point of
the mixture, in an inert solvent such as toluene, xylene, di-
. .
methylformamide or dimethylsulfoxide. Suitable bases are al-
kali met~ll or alkaline earth metal carhona-tes or hydroxides or
. _ 4
', , .
-- . - - .~ , :
:-~ , . : .
~ ':

HOE 7G/F 200
11081~8
terti.ary organic amines such as pyridine or triethylamine.
The starting compounds of formulae II and III are known
from literature and are prepared. by known methods.
b, The compounds of formula I can also be prepared by reacting
compounds of formula II with an equivalent or excess amount
of y-valero-lactone of formula IV under basic conditions
at temperatures of from 100 C to 240 C. The reaction
proceeds according to the following scheme:
( 1)n ~ -O- ~ ~ O~I + CH3 ~ base
II IV
:~ (R1)n ~ --o_ ~ -ocH-c~2-c~2-cooKat
~he compounds of formula II are preferably used in the
form of their alkali metal phenolates. The reactioll can be
carried out in the presence or absence of a solvent.
c) The compounds oE formula I thus obtained if desired, can be
transformec1 into other compounds of formula I by generally
known reacti.ons, or example by saponification, e~terifica
tion, salt formation, transesterification, amidation, dehy--
dration, hydration, reduction, or oxidation. Thus, for in--
stance, compounds containing the functional group Z = COOH
. may be transformed into acid halides by means of halogenati.ng
: agents, for example SOC].2, into aMides by means of amines,
into carboxylic acid salts by means of bases and into esters
by means of alcohols
Es.ters can also be obtained by reac-ting the corresponding
acid halide with an alcohol or by alkylation of a sal.~ of the
~ 5 -
:~ ' ' .
~ . .

HOE 76/F 200
1~0~ 8
acid, for example ~ith a halogen compound or a dialkyl sulfate.
Compounds containi.ng the functional group Z = CN can be
obtained, for example, by dehydration of a primary amide (Z =
CONH2) ~ h phosphorus pentoxide, the functional group
,~S
Z = C may be obtained by the addition of hydrogen su].fide
NE~2
to the nitrile group (~ = CN). Likewise the functional group
Z = CONEI2 can be obtained by adding water to the nitrile group
while the functional group Z = -CH2OH can be obtained, for ex-
ample, by reducing an ester function by means of li.thi.um alumi-
10 num hydride. All these methods are generally known and familiar
to the expert.
The c~ounds cf fon~ula I of the invention exhibit a good her~icidal
action m pre-emergeLlce and post-en~rgence application against numerous ~
po.rtant w2ed grasses, such as A~7ena spp. (wild oats) ~lopecurus (annual bl.ac.'~-
grass), Setaria spp., Echinochloa spp., Digitaria spp., Lolium spp. and Poa sp?.; 15 On the other hand, even high doses are well tol~rated b~ dioctyledoncus
crop plants and various cereals so that the co~pounds are suitable for the
selective con~rol of weed grasses in agricultural crops.
The compositions of the invention contain preferahly 2 -
95 % of the active compounds of the formula I. They are custo-
mar1ly formulated as wettable powder~, emulsifiable concentrates,
dusting agents, granules, etc.
Wettable powders are formulations which are uniformly
dispersible in ~ater and wlllch, in addition to th~ active com-
pound, also contai.n diluents or inert materials, wetting agents,
~5 for example, polyoxyethylated alkylphenols, polyoxyethylated
-~ oleylamines or stearylamines, alky].sulfonates or alkylphenyl-
sulfonates and dispersing agents, for example sodium lignin-sul-
- 6 ~

i~OE -/6/F 2C0
~0~
fonates, so~i.um 2,2'-dinaph.hyLrethane-6,6'-disulfonate or
the sodium ~salt of oleyl-methyl-taurine.
Emulsifiable concentrates are obtained by dissolving the
active compound in an organic solvent, for example, butanol,
cyclohexane, dimethylformamide, xylene or even higher-boiling
aromatics, and adding a non-ionic wetting agent, for example,
a polyoxyethylated alkylphenol or a polyoxyethylated oleylamine
or stearylamine.
Dusting agents are obtained by g.rinding the active com
1G pound with finely solids, for example talc, natural clays,
such as kaolin, bentonite, pyrophi.llite or diatomaceous earth.
Granules can be manufactured either by spraying the ac~ive
compound onto ahsorbent, granular inert material or by appylin~
active compound concentrates by means of adhesives, for examp3.e
polyvinyl alcohol, sodium polyacrylate or even mineral oils,
onto the surfaces of carriers, such as sand, kaolinites or gra
nular inert ma~erial. Suitable formulatiorls can alsc be manu-
factured by the customary methods of manufacture of fertilizer
granules, if desired in admixture with fertilizexs.
In the case o~ herbicidal. a~ents, the concentrations of
the acti.ve compounds in the commercial ~ormulations can vary.
In wettable po~1ders, the active compound concentration varies,
for example, b~tween about ~0 % and 95 %, the remainder con-
sisti.ng of one or more of the abovementioned formulation addi-^
tives. In the case of emulsifiable concentrates, the active com-
pound concentration is about 10.% to 80 %. Dust formulations
: usually contain 5 - 20 % of active compound, and sprayable sol.u-
tions about 2 - 20 ~. In the case of granules, the actlve cor,-
29 pound content in part depends on ~hether the active compound is
: - 7 -
'

~IOE 7~)/F 2C0
~0~1~8
in a liquid or solid form and what granulating auxiliaries,
fillers and tlle like are used.
If necessary or desired the commercial concen~rates may be
diluted prior to application in the usual manner, for example
by means of water in the case o~ wettable powders and emulsi-
fiable concentrates. Dusts and granules are generally ready
for use without further dilution. The amoun~ of active ingre-
dient necessary for obtaining the desired result depends on
external conditions such as temperature, humidity, type of soil,
stage of p3ant development etc. It can vary within wide limits
for example between 0.1 and 10.0 kg/ha of active substance but
is preferably between 0.1 and 5 kg/ha.
The following examples illustrate the invention.
..
FO~1ULATION EXAMPLES
~5 E X A M P L E A:
An emulsifiable concentrate is obtained from
~- 15 parts by weiqht of active substance
75 parts by weight o~ cyclohexanone as solvent and
.: .
10 parts by weight of oxethylated nonyl phel1ol (10 EO)
as emulsifier.
E X A M P L E B
. _ _. . .
A wettable powder which is easily dispersible in water is
~ obtained by mixing
;~ 25 parts by weight of active substance
64 parts by weight of quartz containing kaolin as inert material
; 10 parts by weight of potassium lignosulfonate and
1 part b~ weight o~ sodium oleyl-met1lyl-taurine as wetting
and dispersing agent and grinding the mixture in a pin
29 mill.

110~168 HOE 76/E 2~0
E X A M P L E C:
______
A dustlng powder is obtained by mixing
10 parts by weight of active substance and
90 parts by ~eight of talc as inert material
and comminuting the mlxture in a hanmer mill.
E X _ 2~ P L E D:
A granular formul3tion consists, for example o~ about
2 to 15 parts by weight of active su~stance and
98 to 85 parts by weight of inert granular materials such as
attapulgite, ~urniceand quartz sand.
EXAMPIE5 _E PREPARATION
E X A M P L E 1:
__ __
4-[4l-(2 ,4 dichloropheno~ phen~y~~_alerianic acid
20.3 g of 4-(2',4'-dichlorophenoxy~-phenol were dissclved
in 25 ml of absolute ethanol. 2.1? g of meta]lic sodium ~ere
added and after dissolution of the sodium the ethanol was dist~l-
led off. Nextl 10 g of y-valerolactone were added to the solid
4-(2',4'-clichlorophenoxy)-phenol sodium and the whole was heated
for 24 hours at 210 C. The reaction mixture was then acidified
with concentrated hydrochloric acid and the residue dissolved
in toluene The toluene phase was repeatedly extracted with
saturated a~ueous-methanolic bicarbonate solution (50 ~ strengt.rl~.
The combined extracts were acidified with concentxated hydro-
chloric acid and extracted with toluene. After xemoval of the
solvent under ~educed pressure and recrystallization Lrom cyc1o-
hexane~23.9 g = 80 ~ of the theory of 4-[4'-(2",4 ~dichloro-
phenoxy~-pllenox~-valeric acid melting at 88 C were obtained
C 1~ o ~ c~ c r~ _ C 7 ' C ~ } '~ O C ' i
_ g _
,
~'' ~' ' ,
,

~L~081Çi8
The following com;~und~ were pr~pared in analogous manr.er:
2) ~-[4'-(4"-chloro2heno~y)-phenoxyl-valeric acid melting at
65 - 66 C.
E_A A M P L E 3:
4-[~ 4'l-dichloro~henoxy)-phenoxy]--Jaleric acid butyl ester
25.9 g of 4-(2',4'-dichlorophenoxy~-phenol and 1'l.5 g of
potassium carbonate iII 150 ml of dimethyl for~amide were rerlui:-
ed for 1.5 hours. 20 g of 4-chlorovaleric acid butyl ester wer2
then added dro~wise at 80 C and the mixture ~7as he~ted for 12
hours to 120 C. A~ter filtering off the precipit~ted salt, the
soivent was distilled off under reduced pressure. The oily xesi-
due w~s talsen up in toluene, washPd wi~h dilute sodium hydro~
~olu~ion nd water and dried~ A~ter removal of the toluene unde~-
r:educPd pressure the residue was distilled in hlgh vacuum. 32.1
~ = 78 % of the theory of 4-[4'-(2",4"-dichloropAenoxy)-phenoxy~-
- valeric aci~ butylester boiling at 206 C/0.02 bar were obtained.
:,.'.'~
C~l
C.~ ^-O--C'~ C~:2(~Zl2--c~
Cl \ C~2C~I2C~ CH3
Using 4-chlorovaler~nitrile t:he ~llowin~ c~.p~uncl was pre-
pared in analogous manner:
4) 4-~4~-(4"-trifluoromethylpherlo~y)-phello~y] valeronitrile~
E X A M P L ~_ 5:
4 [~ (?.",4"-d~chloroph noxy)-phenox~r]-v ler~c acid n-proay-i es.e~
29 g of 4-[4~-(2",4"-dichlorophenox~y)-pheno~y]-valeric acid
(o. E~ample 1j were ~leated to 60 C together with 30 ml of toluer.e
. and 12 g OL thionyl chloriAe until the developmen~ o~ gai was ter i~
., _ 1
' ~, , ,
~. . .

1108~68
nated. Toluene and thionyl chloride in excess were then distil-
led o~f under reduc~d pressure. The remaining oil was take;l
up in toluene and added dropwise to a solution of 6 y of n-pro-
panol and 8.5 g o~ triethylamine in 50 ml of toluene. After
the addition, stirring was continued ~or 1 hour at 50 C, the
triethylamino-hydrochloride was filtered off and washed with
water. After removal of the solvent, the reaction product w~.s
distilled in a high vacuum. 27.5 g of ~-[~'-(2",4"-dichloro-
phenoxy)-phenoxy]-valeric acid n-propyl ester boiling at 20C C/
0.01 bar were obtainedO
Cl ~ -0- ~ --0-~Ei-CH~CH2-C~
~ Cl \ C~2C~2'~
1~

1108iÇi8
_X A M P L E 6:
~-[~ trifluoromethy~er.o~:~)- heno~y]-?en,a ol-1
20.4 g of 4-[4'-(4'`-trifluorome~hylphenoxy)-pheno~]-va-
leric acid isobutyl ester (0c Example 7) were added dro~wise t~
a suspension of 1.25 g of lithium-aluminum hvdride in 50 ml 0c
ether. When the addition was terminat2d, the mixture was rerl-~
ed for 1 hour ~lhile stirring. 10 ml of ethyl acetate and then
40 ml of water were added slowly. Fina].ly, 2N a2so4 was adde~
while vi.gorously stirring until the aluminum hydroxide preci~i-
tate had dissolved. The ether phase was washed neutral with
sodium bicarbonate solution and ~he solvent distilled off unde-
reduced pressure. After di.stillation in a high vacuum 15.4 g
= 90.5 % of the theory of 4-[4'-(4"-trifluoromethylpnenoxy~-
phenoxy~-pentanol 1 boiling at 174 C~0.07 i~ar were o~tain~d.
CF~- ~ -0~ ~ -0--CH-C~I~Cll2CI-T70-~
. :
E X A M P _ E 7:
1-chloroacetYloxy-4-[4~-(4~-trl.f]~ ~ x~)-phc_o~
pentane
6.45 g of chloroacetyl chloride. were added dropwise at ~ocm
temperature to a solution of 17.0 g of 4-[4'-~4"--trifluoro~ethy~-
phenoxy)-phenoxy]-~entanol-1 and 5.55 g of tri.ethylamine in ~O ~l
of ab.solute toluene. After the addition, sti.rril1g of the mixtu~e
was continued or 1 hour at 50 C, the precipitate was filtered
off, the toluene solution washed with dilute hydrochloric aci.d
and watex and dried. After remo-~al of the solve~t, 18.5 g =
83 % of the theory of 1-chloroac2tylo~y -[4'-(4"-triIluorome~hyl-
- - 12

~`` ~o~
phenoxv)-phenoxy]-pentc.ne were obtained.
C~ Cr'" ct.'2 -C~ 2 -C-C-CU~
The following compounds were prepared in analogous manner:
8) 1-benzoylo~ 4-[4'-(4"-trifluoromethylphenoxy)-phenoxy]~
pentane. :
9) 1 methylsulfonyloxy-4-[4'-(4"-trifluorometllylphenoY~y)-
phenoxy]-pentane.
10) 1-N,N-dimethylcarbamoyloxy-4-~4~-(4"-trifluoromethylpheno~y)-
phenoxy]-pentane.
For the prepa;-ation of the latter compound stirri.ng of the
reaction mixture was continued for about 10 hours at 60 C.
: Further compounds of formula I obtainable accGrding to .h_
. . .
precodil1g ~xamples are listed in the followiny takl~..
,
r
.
13 -
, . "
. . . . .
-
- .

1108168
A B L E: Cll~
O - Cll -C112 -C112- Z
Example I I
No (R)n Z physical prepared accord-
data in~ to Example
11 2,4-Cl2 -COOCH3 4
12 4~Cl -COOCH3 4
13 2,4-C12 -COOC2H5 6
14 2,4-C12 -COOC3H7(i) 6
4-Cl -COOC3H7(n) 7
16 4-C~3 -COOC8Hl7(n) 7
17 4-CF3 -CcH2cH2cl 6
18 4-Cl -COOCH2CH20CH3 7
19 4-CF3 -COOCH2CH20CH3 6
2,4-Cl2 -COOCH2CH20CH3 6
21 4-CF3 -COOCH~CH2Cl)2 6
22 4-CF3 -Coo-(cH2cH2o)2c2H5 7
23 4-CF3 -Coo(cH2)2ocH2(cH2)2 3 7
24 4-CF3 -COO-CH2 - ~) 6
4-CF3 -Cc~l2cH2~l
26 4-CF3 ¦ -CcH2cH2scll3 6
27 4-CF3 -COO ~ Cl 6
28 ~ 4-CF3 ~ -COO-CHz CH=CH2 ~ ~ 6
- 14 -
~f~
~ .
.. . .
. ~:
.
-

~i¢1`8~6~
T A B L E ~cont.)
.
Example (R) _ physical prepared accord-
No. n data ing to Example
29 4-CF3 -C-cH2-c - Cl-l 6
302,4-CI~ -C~ 1~ ~ Cl ~ 6
32 4-CF3 -C
NH-NH2
332,4-C12 -COOMg 1/2
344-Br-2-Cl -COOCH3 4
354-Br-2-Cl -COOCH2-CH(CH3)2 7
r-
. -A
-15-
' ~
.
, , .
. .

J 11~81~ii8
HO~ 76/F 200
~IOLOGICAL EXAMPLES
E X A ~1 P L E I:
Seeds Of grasses were sown in pots and the surface of the
soil was sprayed with compoc;itions according to the invention
in the form of wettable powders in different concentrations.
The pots were placed for 4 weeks in a greenhouse. The result
of the treatment was evaluated according to the scheme of Bolle
(Nachrichtenblatt des Deutschen Pflanzenschutzdienstes, 16,
1964, 92 - 94)
/
Evaluation Damaging action in % on
n~r ~eeds Crops
1 100 0
2 97.5 to ~100~ 0 to 2.5
3 95 to ~ 97.5 ~ 2.5 to 5
`. 4 90 to < 95 ~ 5 to 10
85 to ~ 90 ~ 10to 15
. 6 75 to < 85 ~15 to 25
7 65 to < 75 ~25 to 35
8 32.5 to < 65 ~ ~35 to 67.5
9 0 to <32.5 >67.5 to 100
:
The test resulLs in the following table show that the com--
pounds of the invention exhibit an excellent herbicidal action
even in a very low concentrat:ion in pre-emergel1ce as well as
~: irl pos~-emeIgellce pr~cesses.
- 16 ~

` 1~0~168 HGE_7j/F 2~0
T A B L E 1: ~
_
E~ ple dose - EC SA DI AL
(Xg ~S ~ )
17 2.5 pre
0.6 1 1 1 2
2.5 post
0-6 1 1 1 2
3 2.5 pre 1 1 - 2
0~6 1 1 - 3
- 2.5 post 1 1 - 1
0.6 1 1 - 1
2.8 2l5 pre
0~6
2,5 post 1 1 _
0-6 1 1 ~ 3
16 2.S pre
0-6
2?5 post 1 1 .
- 0~6 1 1 - 1
8 2-5 pre
Ot6 1 1 - 2
2~5 p~st 1 - 1 - 1
0~6 1 1 - 1
13 2.5 p~e 1 1 - 1
0,6
2.5 post
0~6
~ 2.6 ~5 pre 1 1 - 2
;; 0.6 1 1 - 2
2~5 pc~st
Oq6 1 1 - 1
legends: AS -- active substance
.~ . pre = pre-emergence
. post = post-emergence
EC = Echinochloa (barnyard grass)
S~ - Setaria (brlstl.e grass)
DI = Digitaxia (crabgrass~ :
Al. -- Alopecurus (annual blackgrass~
- 17 --
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