Note: Descriptions are shown in the official language in which they were submitted.
~7~5'7
This is a di~ision of the Canadian patent applica~ion
n~ 318,635 filed on Decemhe.r 27, 1978.
The present invention relates to herbicidal compo-
sitions for controlling undesired plant growth.
~ ore particularly, it relates to herbicidal compo-
sitions for controlling undesired plant growth which comprise
a first component (i) which is a compound of the formula (I) :
H3C ~ 11
/ P-CH2~CH2~lH~cooyl/n (I)
Xl/m NH2
wherein, X and Y are same or different and each represents
hydrogen atom, mono- or divalent metal atom, ammonium,
mono-, di- or tri-lower alkylammonium, mono~ di- or
tri-ethanolammnonium or mono-, di- or tri-lower alke-
nylammonium, and m and n represent valencies of X and
Y, respectively, or
an acid-addition salt thereof, and a second component (ii)
which comprise a herbicide or synergist selected from the
group consisting of choline salt of maleic hydragide, a
phenoxy series herbicide, a benzoic acid series herbicide,
2,3,6-trichlorophenylacetic acid or a salt thereoE, (3,5,6-
trichloro-2-pyridyl)oxy-acetic acid or a salt thereof, N
phosphonomethylglycine or a salt thereof, ethylcarbamoyl-
phosphoric acid or a salt thereof, 2 (l-allyloxyam~nobutyli-
dene)-5,5-dimethyl-4-methoxycarbonyl-cyclohexane-1,3-dione,
3-(3,4-dichlorophenyl)-l-methoxy-l-methylurea, 3-amino 1,2,
4-triazole, choline or a salt thereof, and dieth~lamine or
a salt thereof, admixed in an amount of 0.1 to 20 parts by
weight based on l part by weight of the component (i).
It still further relates to herbicidal compositions
for controlling perennial weeds and brush which comprise a
L-isomer of the compound of formula (I) or an acid-addition
i'7
salt thereof and a herbicide or herbicides recited abo~e
In this specification, mono- or di-valent metal
atom means, for example, sodium, potassium, lithium, copper,
magnesium, calcium, zinc, nickel and manganese atom.
Lower alkylammonium means an alkylammonium having
from 1 to 5 carbon atoms such as methylammonium, ethylammo-
nium, propylammonium, isopropylammonium, butylammonium,
isobutylammonium and pentylammonium.
Di-lower alkylammonium includes, for example,
dimethylammonium, diethylammonium, dipropylammonium, diiso-
propylammonium, dibutylammonium and dipentylammonium.
Lower alkenylammonium contain in its respective
alkenyl, for example, 3 or ~ carbon atoms and a double
bond.
Acid to form a salt with the compound of formula
(I) includes inorganic acids such as hydrochloric acid,
sulfuric acid, hydrobromic acid, phosphoric acid, perchloric
acid and nitric acid, and organic acids such as acetic acid,
propionic acid, citric acid, tartaric acid, chloroacetic
acid, trichloroacetic acid and tri1uoroacetic acid.
Cholines mean choline and salts thereof with an
inorganic acid such as hydrochloric acid, phosphoric acid
or carbonic acid, or with an organic acid such as acetic
acid, oxalic acid or ascorbic acid.
Diethylamines mean diethylamine and salts thereof
with an inorganic acid such as hydrochloric acid, phosphoric
acid or carbonlc acid, or with an organic acid such as
acetic acid, oxalic acid or ascorbic acid~
Phenoxy series herbicide includes, for example,
2,~ dichlorophenoxyacetic acid or salts or esters such as
allyl ester ot ethyl ester thereof~ 2-methyl-4-chloropheno-
xyaceti.c acid or salts or esters such as allyl es-ter or
~7~7
ethyl ester thereof, ~-(3,~-dichlorophenoxy)-propionic acid
or salts thereof, 2-(2-methyl-A-chlorophenoxy)propionic acid
or salts thereof, y-(2-methyl-4-chlorophenoxy)butyric acid
or salts thereof, 2-(2,4,5-trichlorophenoxy)propionic acid
or salts thereof and ~-C4-(3,5-dichloropyridyl-2-oxy)phenoxy~
propionic acid or salts thereof.
Benzoic acid series herbicide includes, for example,
2,3,6-trichlorobenzoic acid or salts thereof, 3,6-dichloro-
2-methoxyben~oic acid or salts thereof and 3-amino-2,5-
dichlorobenzoic acid or salts thereof.
In recent years, the grow-th of perennial weeds has
been increasing in pa~y field, upland, orchard and meadow.
The propagation of perennlal weeds by means of
their underground part is so rapid and strong that it may
not readily be con~rolled. In crop land, they propagate
with their clonal propagation organ of the underground part
finely divided and distributed by cultivation, agitation
and movement of soil~ As perennial weeds are generally
large in size and propagate flourishingly and own the basis
of life under the ground, they predominate over crops in
the competition for nutrients, water and lightO Heretofore,
N-phosphonomethylglycine (hereinafter referred to as gly-
phosate) is known as the controlling agent for perennial
weeds, but it has a disadvantage that it is not so effective
for broad-leaved weeds. Therefore, there have bee'n desired
contxolling agents ha~ing a broad weeding spectrum. I-t has
been also a serious problem to control brush in non-crop
land~ meadow and afforested land. For instance, large
perennial weeds such as miyakozasa (Sasa nipponica Makino
et Shibata) and eulalia (miscanthus ~ nensls Andress.) and
brush such as kumaichigo (Rubus crataegifolius Bunge),
chestnut (Castanea crena-ta Sieb e-t Zucc.) and Japanese bush
7~
cranberry (vib~nurn dilata-tum Thunb.) predominate over Japanese
cedar (Crytomeria japonica D. Don) and Japanese cypress
~ obtusa Endl.) in afforested land in the com~
petition for nutrients, water and light. Also at meadow,
the control of brush around there is a pxoblem.
There are few herbicides eEfective for brush because
of difficulty in controlling it. Namely, unlike herbaceous
plants, brush has a hard bark to preven-t the penetration of
controlling agent; it is generally larger than herbaceous
plants; and it has a developed reproduction mechanism, or
brancheseven after defoliation.
While known herbicides are all synthetic substances,
there have been desired readily degradable herbicides in
view of environmental pollution. 2-amino-4-(hydroxy)(methyl)
phosphinoyl butyric acid, which is one of the compounds
represented by formula (I) and hereinafter referred to as
AMPB, in an antibiotic substance obtained by the methods
disclosed in Japanese Patent Pub:Lication Specifications
48-85538 and 49-31890, as laid open to public inspection and
~0 entitled Novel method of producing ~-amino-~-methylphos-
phinobutyric acid)~. The compound has above mentioned
desirable characteristic that is metabolized and degraded
safely in the substance cycle in the nature.
AMPB is known to control wide varieties of phytopa-
thogenic microorganisms at a low concentration an~ may be
used for an agricultural fungicides, as disclosed in Japanese
Patent Publication Specification 49-14644 as laid open to
Public inspection. After further studies on the biological
activities and utilities of the substance, it has been
found that it has a superior herbicidal activity when applied
at about ten times higher concen-tration than for controlling
phytopathogenic microorganisms. Namely AMPB is effective
~7~
for controlling growing perennial weeds and brush by ki~.ling
the underground part by the ~oliar application and by inhibit-
ing strong]y the reproduction.
As i5 clear in formula (I)~ AMPB has an asymmetric
carbon atom at 2-position, and therefore, there e~ist stereo-
isomers, After further studies of upperground part-killing
activity and reproduction-inhibiting activity of AMYBs, the
inventors have found that L-isomer of AMPB (hereinafter
referred to as L-AMPB) has twice stronger activity than
that of AMPB (hereinafter some times referred to as DL-AMPB)
and that the essence of herbicidal activit~ of DL-AMPB resides
in L-AMPB. The mode of action of DL-AMPB has been studied
by using microorganisms and it has been clear that DL-
AMPB inhibits glutamine synthetase competitively [Helvetica
Chemica Acts, 55 , Fase 1, pp 224-239 (1972~]. It may be
considered that DL-AMPB is taken into the enzyme in place
of the substrate as a kind of unusual amino acid and suspend
the function of the enzyme, thus exhibi-ting the herbicidal
acti~ity.
As generally recognized, naturally occuring amino
acids are all L-form, and enzymes comprising the amino acids
have a high speci~icity. It is therefore presumed that,
among DL-AMPB, L-AMPB is taken into the enzyme in place o~
the substrate`and exhibits herbicidal activity. The presump-
tion coincides with the fact that L-AMPB is twice effective
than DL-AMPB.
DL-AMPBs are usually applied in amounts of 50 g./10
are to 1200 g./10 are to perennial weeds of less than 1
meter height, such as wormwoo~ (Artemisia princeps), curly
dock (Rumex Japonicus Houtt.) and purple nutsedge (C~perus
rotundus L.)i 150 g./10 are to 1500 g./10 are to perennial
weeds of more than 1 ~eter height r such as miyakozasa and
eulalia, and small brush such as torch azalea (Rhododendron
Kaempferi Planch.) and kumaichigo; and 300g./10 are to 3000
g./10 are to large bru~h, such as ches-tnut and oak (Quercus
serrata Thunb), and to large stump for controlling the emer-
gence of new buds, by which perennial weeds and woody weeds
may be killed and the xeproduction thereof may be prevented.
The treatment may be possible throughout year, but it is
generally performed in spring or summer at growing stage,
or in autumn.
The following are examples o compounds of formula
~I) and acid-addition salts thereof to be employed in the
invention: AMPB; its sodium, po-tassium, lithium, ammonium,
magnesium, calcium, nickel,manganese, zinc, copper, methyl-
ammonium, ethylammonium, propylammonium, isopropylammonium,
n-butyl-ammonium, allylammonium and ethanolammonium salts,
and the corresponding di-salts; and its hydrochloric, hy-
drobromic, nitric, perchloric, sulfuric, ace-tic, propionic,
citric, tartaric, chloroace-tic, trichloroacetic and tri-
fluoroacetic acid salts. Thereof AMPB and its sodium, di-
sodium, potassium, dipo-tassium, isopropylammonium, n-bu~yl-
ammonium and diammonium salts are preEerred.
From the foregoing description, it is to be
understood that L-AMPB and the salts thereof are especially
preferred.
The AMPBs, particularly the L-AMPBs show'a strong
reproduction-inhibiting activity by foliar application
besides contact killing activity, the effect is not necessarily
satisfactory depending on circumstances. In order to
utilize the superior characteristics of AMPBs, the inventors
have investigated and found -that the translocating weeding
effect, i.e. reproduction~inhibiting effect of AMPBs, which
is one of their ch~racteristics, could be suprisingly enhanced
.AI~ .
byusing them together with a translocating herbicide or slow
acting type herbi.eide, or with a synergist such as choline
or diethylamine. For instance~ as shown in Table 3, 0.025~
of monosodium salt oE L-~PB kills ~0~ of bitter dock (Rumex
obtusifolius L.) but fails to inhibit its reproduction.
0.1% of 2,4-dichlorophenoxyacetic acid (hereinafter
reEerred to as 2,4,-D) brings about the curvature of foliage
of bitter dock but fails to kill it or inhibit its reprodue-
tion. Contrary to these, a mixture of 0.025% o~ monosodium
salt of L-AMPB and 0.1~ of 2,4-D exhibits a synergistic
effect and kills bitter dock thoroughly, thus inhibiting
its reproduction completely. Similar effects may be observed
in case of noshiba (~y~ Japonica Steud.) which is a
perennial weed of Family Gramineae. Namely, 0.05% of mono-
sodium salt of L~AMPB kills 50% of noshiba, which is repro-
duce~ three months after the treatment to such an extent
that is eomparable to non-treated area~ 0.1% of 2,4-D is
almost inef~eetive ~or controlling gramineous weeds. Con-
trary to these, a mixture of 0,05% of monosodium sal-t of
L-AMPB and 0,1% of 2,4-D enhances the activity of the former
remarkably and kills upperground part throughly~ No
reproduetion is observed at all three months after the
treatment. Thus, subtances having auxin like activity
represented by 2,4-D enhanee the contaet killing aetivity
and translocating killin~ activitv of L-AMPB when admixed
therewith, against both broad-leaved and narrow-leaved
perennial weeds, especially with respeet to reproduetion-
inhibiting activity.
Similar resul-ts may be obtained in case of choline
salt of maleic acid hydrazide (hereinafter referred to as
CMH).
Namely, 0,3~ o CMH itself shows almos-t no effee-t
57
killing upperpart and inhibiting the reproduction of bitter
dock. Whereas, a mixture of 0.3~ of CMH and 0.05~ of mono-
sodium salt of AMPB kills about 90~ of upperground part and
yellows the remainin~ leaves which loses the activity and
ceases the suhsequent growth, thus showing no reproduction.
In general, the efEect of I,~AMPB may be enhanced from two
to five times when used in combination with CMH~ Similar
results may be obtained by using mixtures of AMPBs with a
translocating herbicide or with choline or diethylamine as
the synergist, enhancing the eEfects of AMPBs surprisingly.
Another characteristic of mixtures of AMPBs with
the above mentioned herbicides or synergists is to broaden
the species of weeds to be inhibited its reproduction. In
order for AMPBs to show the characteristics of inhibiting
the reproduction at their maximum, it is essential -that
they translocated to the underground part, after the foliar
-trea-tment and before the death of upperground part.
However, in case of weeds showing a rapid killing
effect such as hedge bindweed (_alystegis hederacea Wall.),
the ~oliage gets killed before the translocation of AMPBs,
thus makin~ it difficult to inhibit the reproduction at -the
underground part. When AMPBs are used together with the
translocated herbicide or slow acting herbicide mentioned
above, they enhance the effect of the herbicides, and as
the result, enhibit a superior reproduction-inhibiting
effect against far broader species of weeds than sole use
of AMPBs.
Among mixtures of the invention, the mixture of
AMPBs with CMH is most excellent in view of its broad weeding
spectrum and the thoroughness of effect.
CMH is known to control perennial weeds by autumn
treatment, as disclosed in Japanese Pa-ten-t Publication
Specification 49 55835, as laid open to public inspection.
However, a pra~tical defect of CMH is that the
timely treatment therewith is resticted to autumn and that
cutting of upperground part is required after -treatmen~ when
it is used in spring or summer. If CMH is used in combination
with AMPBs, the latter kill upperground part gradually,
during which period both active ingredients are translocated
to underground part and kill it by a synergistic action.
Thus, the reproduction-inhibiting activity of CMH may be
exhibited at its ma~imum and -the timeliness of treatment
therewith may be extended to throughout year. The practical
utility of CMH has thus been improved.
Still another characteristic of mixtures of AMPBs
with herbicides mentioned above is that -they are quite
effective for controlling bottom weeds of Japanese cypress
afforested land, particularly perennial weeds and brush.
In particular, both CMH and ~MPBs show no phyto-
toxicity to Japanese cypress, and therefore, the combination
is quite useful for the practical control of bottom weeds
of Japanese cypress afforested land.
As described above, the joint use of AMPBs with
the herbicides mentioned above brings about pratically
preferable characteristics, based upon which the following
usages may be considered. Namely, mixtures of AMPBs, with
the herbicides may be used for controlling a wide variety
of annual weeds, perennial weeds and brush, particularly
perennial lowland wee~s in paddy field after harvesting;
perennial weeds in upland before sowing; perennial weeds
and brush in affore~ted land to enable planting; perennial
weeds and brush in meadowi perennial weeds and brush in
non crop land such as factory, railroad, park, public facil-
ities, riverbed, bank, high way, golf links and rested crop
g _
~7~t7
landi and water weeds and algae by means of foliar application
in water.
Like CMH, ammonium ethylcarbamoylphosphate (herein-
after referred to as DPX-1108), cholines and diethylamines
give no phytotoxicity to Japanese cypress, and therefore,
may be used in combination with AMPBs to control bottom
weeds of Japanese cypress afforested land. The mixture
of AMPBs and CMH is also very useful for controlling perennial
weeds in upland before sowing which are difficult to be
controlled.
When AMPBs or L-AMPBs are mixed with other herbicide
recited above, the ratio will vary from 1:0.1-20 by weight;
but it will vary depending on the herbicide to be mixed
therewith, as indicated in the following Table 1. Upon
application, the composition may be diluted with water to
a concentration indicated in the Table and treated at a
rate of from 25 to 250 li-tre per 10 are, preferably from
50 to 150 litre per are.
-- 10 --
7~57
TABLE 1.
___ . _ . __
.Mi~ing ratio Applica-tion
Composition (wt.~ concentration ~%)
AMPBs 1 0.01-1.0
: CMH 1 : 1.0 10.0 ~ : 0.2 - 1.0
: NP- 48 1 : 0.5- 5.0 )~: 0.05 - 0.5
>3 : SL-501 1 : 0.5- 5.0 : 0.05 - 0.5
: 2,4-D 1 : 0.2- 4.0 : 0.05 - 0.4
: Dowco~233l- 1 : 0.1- 3.0 : 0.02 - 0.2
: linuron 1 : 0.4- 4.0 : 0.05 - 0.5
: DPX-1108 1 0.5- 5.0 ~: 0.1 - 0.6
: glyphosate 1 : 0.3- 3.0 ; 0.03 - 0.5
: cholines 1 : 1.0- 2.4* : 0.01 - 0.8
: diethylamines 1 : 1.0- 2.4* : 0.01 - O.S
L-AMPBs : CMH 1 : 1.0-20.0 0.005-0.5 : 0.005-10.0
: 2,4-D 1 : 0.3- 8.0 : 0.0015- 4.0
: MCP 1 : 0.3- 8.0
: 3,4-DP 1 : 0.5- 8.0 : 0.0025- 4.0
: MCPP 1 : 0.3- 8.0 : 0.0015- 4.0
: MCPB 1 0.3- 8.0 :
: 2,4,5-T 1 : 0.3 -8.0
: SL 501 1 : 0.5-10.0 : 0.0025- 5.0
~ 2,3,6-TBA 1 : 0.3~ 8.0 : 0.0015- 4.0
> : Banvel-D~ 1 ~ 0~3- 8.0 ,
: amiben~ 1 : 0.3- 8.0
: TPA 1 0.3- 8.0
: Dowco-233 1 : 0.2- 6.0 : 0.001- 3.0
: glyphosate 1 : 0.3- 5O0 : 0.0015- 2.5
: DPX-1108 1 : 0.5-20.0 : 0.025-10.0
: NP-48 1 : 0.5-15.0 : 0.0025- 7.5
: linuron 1 : 0.5-15.0 )> :
t (trade ~ark)
-- 11 --
~7~
TABLE 1. (Cont.)
_
. .Mixing ratio Application
Composltlon (wt.) concentration ~)
L-AMPBs : ATA 1 : O.3-10.0O.005Ø5 : O.0015-5.0
~ cholines 1 : 0.5- 5 : 0.0025-2.5
: diethylamin~es1 : 0.3- 3~> : 0.0015-1.5
* molar ratio
NP-48 : 2-(1-all~loxyamino butylidene)-5,5-dimethyl-
4 methoxycarbonylcyclohexane-1,3-dione
SL-501 : a-~4-(3,5-dichloropyridyl-2-hydroxy)phenox~ -
propionic acid
Dowco-233 : 3,5,6-trichloro-2-pyridyloxyacetic acid
linuron : 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea
MCP : 2-methyl~4~chlorophenoxyacetic acid
3,4-DP : ~-~,4-dichlorophenoxy)propionic acid
MCPP : 2-(2-methyl~4-chlorophenoxy)propionic acid
MCPB : r- (2~mekhyl 4-chlorophenoxy)butyric acid
2,4,5-T 2-(2,4,5~trichlorophenoxy)propionic acid
2,3,6-TBA : 2,3,6-trichlorobenzoic acid
Banvel-D : 3,6-dichloro-2-methoxybenzoic acid
amiden : 3-amino-2,5-dichlorobenzoic acid
TPA : 2,3,6-trichlorophenylace~ic acid
ATA : 3-amino-1,2,4-triazole
AMPBs or L-AMPBs, or mixtures thereof ~ith above
mentioned herbicides or synergists may be formulated into
water-soluble powder, liquid formulation, wettable powder,
emulsion, dust or granules with appropriate diluents. The
formulations may contain surfac-tants such as polyoxyethylene
octylphenyl ether, polyoxyethylene dodecyl ether, polyoxy-
ethylene fatty acid ester and polyoxyethylene alkylaryl
et~ler to improve spreading, adhesion and dispersion and -to
- 12 -
enable certain and enhanced effects.
The following are examples of formulation by which
the scope of the invention may not be restricted :
Formulation l. Liquid formulation
30.0 % by weight of monosodium salt of AMPB, 15.0%
of polyoxyethylene octylphenyl ether, 0.15% oE methyl p~
hydroxybenzoate and 54.85% of water are mixed and dissolved
to make the formulation. Upon application, it is diluted
with water and subjected to fGliar treatment.
Formulation 2. Wetta~le powder
50.0~ of monosodum salt of L-AMPB, 45.0% of dia-
tomaceous earth and 5.0% o~ nonionic/anionic surfactant
are finely pulverized and mixed homogeneously to make the
formulation.
Upon application, it is diluted with water and
subjected to ~oliar treatment.
Formulation 3 Dust
5.0% of monoisopropylamine salt of AMPB, lO.0 ~
of CM~ and 85.0~ of talc are pulverized and blended homo-
~eneously to make the formulation. Upon application, it
is subjected to foliar treatment, as such, in amount of
0.4-6 kg. per lO are.
Formulation 4. Liquid formulation
10.0% of monosodium salt of L-AMPB, 20.0% of CMH,
15.0~ of polyoxyeth~le~e octylphenyl ether, 0.15~of methyl
p-hydroxybenzoate and 54~85% of water are thoroughly mixed
and dissolved to make the formulation. Upon application,
it is diluted with water and subjected to foliar treatment.
The following are examples of the invention.
EXAMPLE 1
Salts of DL-AMPB or L-AMPB or mixtures thereof
with CMH were diluted to co~centrations indicated in Table 2
- 13
7~7
and sprayed by foliar application -to bitter dock trans-
planted to pots of diameter 20 cm. in amount of lO0 litre
per are~ .
Killing index of upperground part after 21 days
(O:no effect, 5:death) as well as killing index and repro-
duction-inhibiting effect at underground part after 4
months (-:no reproduction, +~+:maxium reproduction) were
determined.
The detail of this assessment made in this Example
was as follows :
Killing indexFoliage Damage (%)
O O
l 20 %
2 40 %
3 ~0 %
4 80 %
lO0 %
Four months after treatment, evaluation was made
for inhibition of reproduction expressed in -terms of symbols
ranging from (-) to (+-~) where (-) means no reproduction,
namely complete suppression of reproduction, (~ remarkable
suppression of reproduction, (+) considerable suppression of
reproduction; (~+) medium suppression of reproduction; and
(+++) no suppression of reproduc-tion.
As the surfactant, 0.1% of polyoxyethylene octyl-
phenyl ether was added to each spraying solution. The
results are shown in Table 2.
- 14 -
57
TABLE 2.
. 21fdays After 4 months
AMPB concentration (wt. %)
0.025 0.05 0.025 0.05 .
. ~
DL-AMPB Na salt O 2 O +++ O +-~+
~> di-Na salt 0 2 0 +-~+ 0 +++
K salt 0 2 0 +++ 0 +++
)> di-K salt 0 2 0 +~ 0 -~++
i-PrNH2 salt 1 2.5 0 +~-~ 0 +-~+
)~ n-BuNH2 salt 1 2.5 0 +-~+ 0 +++
. .,..... _ _
L-AMPB Na salt 2 3 O -~+ 2 ++
di-Na salt 2 3 0 +-~+ 2 -~
L salt 2 3 0 +-~+ 2 -~-~
di-K salt 2 3 0 +++ 2 ++
i-PrNH2 salt 2.5 3.5 0 +++ 2.5 +
n-BuNH2 2.5 3.5 0 ++-~ 2.5 ++
CMH (0,3%) 1 0 ++-~
DL-AMPB Na + CMH (O,3~) 2 3 5 1 +-~-~ 4 +
di-Na + 2 3.5 1 -~+-~ 4
K + 2 3.5 1 ~ 4
di-K + 2 3.5 1 -~-~+ 4 -~
i-PrNH2 + 2.5 4 1.5 +++ 4.5 -~
n-BuNH2 + 2.5 4 1.5 -~++ 4.5 ~
L-.~MPB Na + CMH (0,3%) 3.5 4.5 4 + 5 _
di-Na + 3.5 4.5 4 + 5
K ~ 3.5 4.5 4 ~ , 5
di-K + 3.5 4.5 4 + 5 _
i-PrNH2 + 4 5 4.5 + 5
n-BuNH2 + 4 5 4.5 + 5
_ _ __ _ _
None 0 0 +++
As shown in Table 2, 0.05% of DL-AMPB alone killed
upperground part after 21 days considerably, while 0.5~ of
L-AMPB alone not only killed upperground part after 21 days
~7:~57
and 4 months considerably bu-t also inhibi-ted the reproduction
to some extent. I'he mix-tures of L-AMPB with CMH exhibited
about twice killing and reproduction-i~hiblting effects as
compared with the m:i.xtures of DL-AMPB with CMH~ In comparison
of the mixtures of L-AMPB with CMH against L-AMPB alone,
0.025% of L-AMPB killed 40-50% of bitter dock after 21 days
but failed to inhibit the reproduction. 0.3% of CMH showed
neither killing effect nor reproduction-inhibiting effect.
Whereas, the mixtures of 0.025~ of L-AMPB with 0.3~ of CMH
killed 80-90% of bitter dock after 4 months, yellowed the
remaining leaves and deprived them of the activit~, finally
leadin~ to the death an~ inhibition of reproduc-tion. As
mentioned above, the effects of the mixtures of L-AMPB with
CMH were more remarkable than the mixtures of DL-AMPB with
C~H, which however, could be used sufficiently for the prac-
tical control of bitter dock.
EXAMPLE 2
Naturally growing bitter dock whic is several
years old after germination and noshiba which is a perennial,
gramineous weed were transplanted to pots. After taking of
roots, each spraying solution indicated in Table 3 was sprayed
by foliar application in amount of 100 litre per 10 are.
Killing index after 21 days and reproduction-inhibiting
e~fect effect after 3 ~onths were determined in accordance
with the same evaluation standard as in Example 1, and the
results are shown in Table 3. In the Table, A means sodium
salt of DL-AMPB anfl LA means sodium salt of L-AMPB.
- 15 -
~7~
TAsLE 3.
After 21 days Ater 3 months
Concen :ra~ion (%) bitter ~ hib~ bitter r~n-h'b;~
A 0.05 2 1.5 -~+-t +-~+
0.1 3.5 2.5 -~t ++
2,4-D 0.1 1 0 -t+-t +++
Na salt
0.2 2 0 ++~ +++
)> 0.1 ~ A 0.05 5 3.5 +-~ ++
+ 0.1 5 4 + +
0.2 + 0.05 5 4.5 _ _
+ 0.1 5 4.5
CMH 0.3 0 0 ++-~ +*
0.6 0 0 ~ +*
0.3 + A 0.05 4.5 3.5 _ _
+ ~> 0~1 4.5 ~ _ _
0.6 + 0.05 5 5 _
+ 0.1 5 5 _ _
DPX-11080.15 0 0 ~+~ +-~*
ammonium
salt
0.3 0 0 ~++ ~*
0.15 + A 0.05 1 2 ~ ~
+ 0.1 1 2.5 + +
0.~ + 0.05 4 4 _
+ 0.1 4 4.5 _ _
SL-501 0.15 1 2 +++ +-t
Na salt
0.3 1 3 +++ ~+
0.15 + ~ 0.05 2 4 ~+ +
+ 0.1 2 4.5 ++ +
0.3 + 0.05 3 ~.5 ~
+ 0.1 3 5 ~ _
Dowco~233 0.05 3 0 + +++
triethylamine
salt
0.1 4 O + +,~+
0~05 ~ ~ 0.05 5 2.5 + +
+ 0.1 5 3 + +
0.1 + 0.05 5 5 _
+0.1 5-l7 5 _ _
7~5~
NP-48 0.15 1 2 .~ ~+
0.3 1 3.5 ~ ++
0.15 + A 0.05 2 4 ++-~ + .
,~ + 0.1 . 2 ~ ++ +
0.3 ~ >~ 0.05 3 ~.5 +
+ 0.1 3 5 +
linuron 0.1 4 2 -~++ -~++
0.3 4 5 ~ +++
0,1 + A 0.05 5 3 ++ +
+ 0.1 5 5 ++ +
0.3 + 0.05 5 ~ _
+ 0.1 5 5 _
glyphosate O . 05 1.5 1 ~ +++
i sopropyl -
amine salt
0.1 2.5 2 ++ ++
0.05 + ~ 0.05 4 3.5 .~ +
-~ 0.1 5 5 _
0.1 + 0,05 5 4.5 _
+ 0.1 5 5 _
choline 0.1 0 0 +++ +~+
.~CQ
0.2 0 0 +~+ +++
0.1 + A 0.05 3.5 3 + +
+ 0.1 4.5 4 _ _
0.2 + 0.05 5 5 _
+ 0.1 5 5 _ _
diet.hylamine
.HCQ0.1 0 0 +++ -~++
0.2 0 0 +++ ~++
0.1 + A 0.05 3 2.5 + +
+ 0.1 4 4 _ _
0.2 + 0.05 5 5 _ , _
+ 0.1 5 5 _
LA 0.025 2 1.5 +++ +++
0.05 3.5 2.5 ++ +++
CMH 0.3 0 0 +++ +-~ *
0.6 0 0 ~-~+ + *
0.3 + LA 0.025 4.5 3.5 _ _
0.3 + 0~05 4.5 4 _
0.6 + 0.025 5 5 _ _
0.6 + 0.05 5 5 _
- 18 -
71~7
2,4-~ 0.1 1 0 ~-~+ +++
Na Salt
~, 0.2 2 0 ~++ ++*
0.1 + LA 0.025 5 3.5 _ +
0.1 + ~> 0.05 5 5 _
0.2 + 0.025 5 5 _
0.2 + 0.05 5 5 _
MCP 0.1 1 0 -~++ ~++
Na salt
0.2 2 0 ++~ +++
>~ 0.1 + LA 0.025 4.5 3 + +
0.1 + ~ 0-05 4.5 4 _ _
0.~ + 0.025 5 5 _ _
0.2 -~ 0~05 5 5 _
3,4-DP 0.1 1 0 +++ +++
0.2 2 0 +~ +++
0.1 + LA 0.025 4 3
0.1 + 0.05 4 4.5 _
>~ 0.2 + 0.025 5 5 _
0.2 + 0.05 5 5 _ _
MCPP 0.1 1 0 ~-~+ +++
Na salt
0.2 2 0 +~+ ~++
0.1 + LA 0.025 4.5 3 +
0.1 + 0.05 4.5 4 _
~> 0.2 + 0.025 5 5 _
)~ 0.2 -~ ~> 0.05 5 5 _
MCPB 0.1 l 0 ~++ ~+
Na salt
0.2 2 0 +~+ +++
0.1 + LA 0.025 4.5 3 + +
0.1 + 0.05 4.5 4 _
0.2 + ~> 0~025 5 5 _ ,
0.2 + 0.05 5 5 _
2,4,5-T 0.1 1 0 ~ ~++
Na salt
0.2 2 0 +++ ++~
~ 0.1 + LA 0.025 4.5 4 +
0.1 + 0.05 4.5 4 _
0.2 + 0.025 5 5 _
0.2 + 0.05 5 5 _
SL-501 0.1 0.5 2 ~+f, ++
salt
-- 19 ~
SL-501 0.1 0.5 2 ~ ++
Na salt
~, 0.2 2 3 ~+~ ++
0.1 ~ LA 0.025 2.5 4 ~+
0.1 ~ 0.05 3.5 4.5
0.2 -~ 0.025 3.5 4.5
0~2 + 0.05 4.5 5
2,3,6-TBA 0.1 1 0 ~++ ++-~
Na salt
0.2 2 0 +++ +++
0.1 + LA 0.025 4 3 + +
0.1 -~ 0.05 ~ 3 _
0.1 + 0.025 5 5 _
0.2 + 0.05 5 5 _
Banvel-D 0.1 1 0 +++ ~+
dimethylamine
0.2 2 0 -~++ +~+
0.1 + LA 0.025 4 3 ~
0.1 + 0.05 4 4 _
0.2 + 0~025 5 5 _ _
0.2 + )~ 0.05 5 5 _ _
Amiden 0.1 1 0 ~++ +++
Na sal-t
0.2 2 0 ~ +++
0.1 -~ LA 0.025 4 3
0.1 + 0-05 4 3 _
0.2 + 0.025 5 5 _ _
0.2 + 0.05 5 5 _
TPA 0.1 1 0 +f-~ +~+
Na salt
" 0.2 2 0 ++~ +~
0,1 ~ LA 0.025 4 3 + +
TPA 0.1 + LA 0.05 4 3 _
Na salt
0.2 + 0.025 5 5 _
0.2 + 0.05 5 5 _ _
Dowco-233 0.05 3 0 ~ ~++
triethylamine
salt
~> 0.1 4 0 ~ -~++
0.05 ~ LA 0.025 5 2.5 ~ +
- 20 -
Dowco-233
triethylamine
salt
0.05 ~ LA 0.05 5 3.5 _ _
0.1 + 0.025 5 5 _
~.1 + )> 0,05 5 5 _ _
glyphosate 0.05 1.5 1 ~++ ~+
isopropyl-
amine salt
0.1 2.5 2 ++ ++
0.05 + LA O.U25 4 3.5 + t
0.05 + 0.05 5 5 _
0.1 -~ 0.25 5 4.5 _ _
O L 1 + 0.05 5 5 _
DPX-'108 0.2 0 0 +++ ++*
ammonium salt
0.4 0 0 +~-~ +*
0.2 + LA 0.025 2 2.5 + +
0.2 + 0.05 3 3.5 _
0.4 + 0.025 4.5 4.5 _ _
0.4 + 0.05 4.5 4.5 _
NP-48 0.15 1 2 +-~-~ ++
0.3 1 3.5 ~++ +~
0.15 + LA 0.025 2.5 4 ~I
0.15 + 0.05 3 4.5 ~
0.3 + 0.025 3.5 5 _ _
0.3 + 0.05 4 5 ~
linuron 0.1 3 2 ~*+ +++
0.3 4 4 +++ +++
0.1 + 0.025 5 4 ++ +
0.1 + 0.05 5 5 _
0.3 + 0.025 5 5 _
0.3 + 0.05 5 5 _
ATA 0.05 2 2 -~++ ~+
0.1 4 4 +++ +-t-t
0.05 + LA 0.025 4 4 ++~ +
0.05 -~ 0.05 5 5 _
~> 0.1 + 0.025 5 5 _
0.1 + 0O05 5 5 _
choline 0.1 0 0 +-t+ ~++
.HCQ
~, 0.2 0 0 ~++ ~+
21 -
7~
choline
" o.l + LA 0.025 3.5 3 ~
,> 0.1 ~ 0.05 ~.5 ~ _ _
>~ 0.2 ~ 0.025 5 5 _
0.2 + 0.05 5 5 _
diethyl- 0.1 0 0 ~+~
amine.HCQ
0.2 0 0 -~+~
0.1 -~ LA 0.025 3 2.5 +
0.1 + ~> 0-05 4 4 _
0.2 + 0~025 5 5 _
0.2 + 0.05 5 5 _
None 0 0 +++ +++
* suppression of elongation of upperground part.
EXEMPLE 3
Sodillm salt of DL-AMPB, L-AMPB, CMH or mixtures
thereof were diluted and sprayed by foliar application to
naturally growing perennial weeds in amount of 150 litre per
lO are.
Each spraying solution contained 0.1~ of polyoxy-
ethylene octylphenyl ether as the surfactant. Killing index
after 21 days and reproduction-inhibiting effect after 4
months were determined in accordance with the same evaluation
standards as in Example l and the results are shown in Tables
4 and 5. In the Tables, symbols A, B, C~ D, E, F, G, H, I
and J have the following meanings
A : azumanezasa
B : wormwood
C : bitter dock
D : yabugarashi
E : needle grass
F : kudzu
G : inuwarabi / I : purple nu-tsedge
~l : warunasubi / J ~ hcdge bindweed
S7
_ + + + + + ^t I , , , , , -t
H + + +t + + -t + + + , ~, , , t
. I
~ + + + + + + + + I I I , +
_
~ + + ++ , , , + -~ + + , , , , +
+ + ~,, t + + -~ +
h ~ + + I ~1 . I + t+, +, , , , , +
~ _
L~ + + + + ~ ~
~ ~ + + -t -+ -+ + + + +, ~,, , +
_ _~L-
U + + + I I I +
+ + I I + + I I I +
m + , , , + ~ , , , ' ' ' +
+ + , , :t + + , , , , , ++
_ . I
r ~ Ln Ln Ln Ln ~l r~ Ln Ln Ln Ln Ln Ln o
~:1 H ~J ~ r~ ~ O o ~ ,J ~r ~r Ln Ln o
m ~ Ln Ln Ln Ln
E~ ~ ~ ~r Ln Ln o ~ ~ r ~r Ln Ln o
0 _ , . ~ . . _ _ _ _ . I
~ ~ ~ p o o ~ Ln Ln o
,~ ~ ~ Ln Ln Ln O ~1 ~ Ln Ln Ln Ln Ln O
~ _ ~r Ln
h~1 r Ln LnLn o~1 ~r Ln Ln Ln Ln Ln o
L ~ ~ ~r Ln n o~l ~ ~r ~rLn Ln L~ o
U ~ r LnLn o o ~r Ln, Ln Ln Ln Ln o
~r _
m ~r LnLn Ln ~ Ln Ln Ln Ln n Ln o
Ln
~r LnLn o ~ ~ ~r ~rLn Ln Ln o
- - - -
~ ~O ~ ~D ~ ~
d~ O O O O O O
- ~ ~:
~ + -~ + + + +
~ ~ ~ ~ Ln
~ o o o o o o o o o
u m m m
æ
23 --
~7~7
~ t
~ I :t + -+~ ++ :t + , , , , , , :~
--r -
~
H .~ .1. .~ + .~ .~ _,L, + .,~
_ + + ~ + +l I
+ +
:t ++ + ~ ~ .,, ,, ++
_ _ + +
U~ +,I,,.......... +++,,,,~
~: -'- -1-
_ + ~ +l, + :t + +,,,,, -+
~ + -~ +
~ ~ + +, +,, -+ -t +, +,, , I , -+
IH ¦ .
~ ~ ++ + ++ + + + + +
.... + + + + + + + + +1 '-~1 1 1 + "'
~,+ -+ :t + `
_ + + , , + + , , , , , ,_+ I ,
m + I I I -+ + I I I I I I +
_ _ . _
_ ~+II+,..+IIIII+
1~ Ln Ln Ln Ln ~ ~ Ln Ln Ln Ln Ln Ln o
_ I
Ln H Ln Ln
~ 1 ,~ "~ o o N N ~r~r Ln Ln O
m . _
~ ~ ~ ~ n Ln o ~ ~~l n Ln ~n Ln o
E~ _
~ Ln
~ L~ r o o ~r~ r Ln ~n o
~, _,. . . I
ra ~ Ln
~ ~ ~, Ln Ln o ~ ~rn n n ~n n o
N ~
~o _ ~r n ~n ~n o ~ n n n Ln n o
~ ~ . In
~') d' n ~n o ~~ ~ ~ n n Ln o
~ --
c~ ~n
~ nLn o o ~ ~ ~n n ~n n o
m ~r n ~n n ~ Nn n n n n n o
f~ n
N ~r n Ln o N ~ ~ n n n o
__ n
N n
O O r-lN ~ LD ~ LD ~ D ~ LD
o\ OOOOOOOOOOOO
~ C~
+ + + + -~ +
.L~ N n
~ o o ~
o o o o
o ~m
-- 24 --
~7:~7
As shown in Tables 4 and 5 the reproduction-inhihiting
a~tivity of AMPB was surprisingly enhanced and khe weeding
spectrum was broadened by mixing it wi-th CMH.
EXEMPLE 4.
.
Sodium salt of DL-AMPB, L-AMPB, CMH or mixtures
thereof were diluted and sprayed by Eoliar application in
amount of 150 litre per 10 are at Japanese cypress afforested
land.
Killing index after 30 days and 3 months was deter-
mined in accordance with the same evaluation standard as in
Example 1, and the results are shown in Tables 6 and 7.
TABLE 6
_
After 30 days A-fter 3 months
Concentration (%) _ _
K L M N O K L M N O
DL-AMPB 0.125 0 5 3 3 4 0 4 2 2 3
0.25 0 5 4 4 4 0 5 3 3 4
0.5 0 5 5 5 5 0 5 4.5 4.5 5
CMH 0.25 0 0 0 0 0 0 0 0 0 0
0.5 0 1 1 1 1 0 0 1 1 1
'> 1.0 0 3 3 2 2 0 1 2 1 2
DL-AMPB 0~125 + CMH 0.25 O 5 3 3.5 4 O 5 4.5 4 4.5
+ 0.5 0 5 4 4 4.5 0 5 5 4.5 5
+ 1.0 0 5 4 4 4.5 0 5 5 5 5
0.25 + 0.25 0 5 4.5 4.5 4 0 5 5 4.5 5
+ 0.5 0 5 5 5 5 0 5 5 5 5
+ ~> 1.0 0 5 5 5 5 0 5 5 5 5
>~ 0.5 + ~> 0.25 0 5 5 5 5 0 5 5 5 5
+ 0.5 0 5 5 5 5 0 5 5 5 5
+ >~ 1.0 0 5 5 5 5 0 5 5 5 5
None 0 _ 0 0 0 0 0 0 0 0
- 25 -
T~BLE 7
._
. ~ __ _ _I
After 30 days After 3 months
Concentration t%) _ _
_ _ _ K L M N O K L M N O
L-AMPB 0.063 O 5 3 3 4 O 4 2 2 3
0.125 0 5 4 4 4 0 5 3 3 4 ,
?> 0.25 0 5 5 S 5 0 5 4.5 4.5 5
CMH 0.25 0 0 0 0 0 0 0 0 0 0
0.5 0 ~ l l l 0 0 l 0 l
l.0 0 3 3 2 2 0 l 2 l 2
L-AMPB 0.63 + CMH 0~25 0 5 3 3.5 4 0 5 4.5 4 4.5
+ 0.5 0 5 4 4 4.5 0 5 5 4.5 5
" + 1.0 0 5 4 4 4.5 0 5 5 5 5
0.125 + 0.25 0 5 4.5 4.5 4 0 5 5 4.5 5
~ 0.5 0 5 5 5 5 0 5 5 5 5
~ 1.0 0 5 5 5 5 0 5 5 5 5
0.25 ~ 0.25 0 5 5 5 5 0 5 5 5 5
+ 0.5 0 5 5 5 5 0 5 5 5 5
-~ 1.0 0 5 5 5 5 0 5 5 5 5
20 None 0 0 _ _ 0 0 0 0 0 0
K : Japanese cypress
L : chestnut
M : miyakozasa
N : eulalia
O : kumaichigo
26 -
57
EXAMPLE 5.
Sodium salt of DL-AMPB or CMH, or mixtures thereof
were sprayed by foliar application to shrubs of about 60-70 cm.
height indicated in Table 7. Each spraying solution contained
0.1% of polyoxyethylene octylphenyl ether as the surfactant.
Killing index after 21 days and reproduction inhibiting
effect after 4 months were determined in accordance with the
same evaluation s-tandards as in ~xample 1, and the results
- are shown in Table 8.
T~L~ ~
After 21 days Af-ter 4 months
Concentration (%~ _ _ ~
W X Y Z L W X Y Z L
_
DL-AMPB 0.1 4 4 0 1 4 + + +++ +++ ~
0.2 5 5 0 2 5 ~ _ +++ + _
0.4 5 5 0 4 5 _ _ ~ t _
CMH 0.3 0 0 0 0 0 ++ ~ +++ + ~
0.6 0 0 0 0 0 ~ ~ ~++ _ _
DL-AMPB 0.1 + CMH 0.3 5 5 0 2 5 _ _ ~ + _
+ 0.6 5 5 0 2 5 _ _ +++ _ _
0.2 + 0.3 5 5 0 3 5 _ _ +++ _ _
+ 0.6 5 5 0 3 5 _ _ +++ _ _
0.4 + 0.3 5 5 0 4.5 5 _ _ +~+ _ _
+ ~ 0.6 5 5 0 4.5 5 _ _ ++-~ _
None 0 0 0 0 0 0 ~++ ++-~ _ _ +++ +++
W : Japanese red pine (Pinus densiflora Sieb. et.
Zucc . )
X : Japanese larch (Larix Leptolepis Murr~
Y : Japanese cypress
Z : Japanese cedar
L : chestnut
- 27 -
EXEMPLE 6
Sodium sal-~ of DL-~MPB, L-AMPB, C~IH, or mixtures .i
thereof were sprayed by foliar application to naturally
growing shrubs on October 25, in amount of 150 litre per 10
are.
Each test area was 4 m2 and each spraying solution
contained 0.1~ of polyoxyethylene octylphenyl ether as the
surfactant. The reproduction-inhibiting effect was determined
on May 23 of the next year in accordance with the same
evaluation standard as in Example 1. The xesults are shown
in Tables 9 and 10.
TABLE 9
.
Reproducti.on-
Concentration (~)inhibiting .Remarks
effect
. _
. DL-AMPB Na 0.125 3.5 A'=5, B'=3, U=5, A=4.5
~' 0.25 4 C'=5, Dl=~.5, B'=3.5
0.5 5 A'=5, D'=5, U=5
20 CMH 0.5 0.5-1 D'=0.5, U=1.5-2, E'=1.5
1.0 1 C'=3.5-4, U=3.5-5,
D'=0.5, others =
slightly inhibi-ted
~, 2.0 1-1.5 L=3.5, D'=l, F'=l,
others=slightly
inhibi-ted
DL-AMPB Na 0.125 ~ CMH 0.54.5 almost not reproduced
A=4.5-5 '
-~ 1.0 4.5 H~, U and A=almost
not reproduced
" + 2.0 5 A, B', A', L' and
_ _ others ~nhibi-te
- 28 -
~7~i7
TABLE lO
. Reproduction- . .
Concentration (%) inhibiting Remarks
. . effect
L-AMPB Na 0.625 3.5 A'=5, B'=3, U=5, A=4.5
>~ 0.125 4 C'=5, D'=4.5, B=3.5
~3 0.25 A~=5, D'=5, U=5
CMH 0.5 0.5-1 D'=0. 5, U=1.5-2, E'=1.5
~> 1.0 1 C'=3.5-4, U=3.5-4,
D'=0.5, others =
. slightly inhibited
2.0 1-1.5 L=3.5, D'l, F'=l,
others=slightly
. inhibited
L-AMPB Na 0. 0625 + CMH 0.5 4.5 almost not reproduced
incl. of G' and E',
A=4.5-5
+ 1.0 4.5 H'~ U and A=almost
not reproduced
+ 2.0 5 A, B', A', L' and
others=inhibited
L-AMPB Na 0.125 ~ CMH 0.5 4.5 D', U, A and B'=
almost not reproduced
?> + 1.0 4.5 B', U, D~=almost not
reproduced
+ 2.0 5 not reproduced .
L-AMPB Na 0.25 + CMH 0.5 5 H'=slightly resistant
others=not reproduced
+ 1.0 5 not reproduced
~ 2.0 5 not reprodu,ced
None 0 A'=30 cm, H'=20 cm,
D'=50 cm, A=75 cm,
U=10=20 cm, B'= 25 cm.
DL-AMPB Na 0.25 + CMH 0.5 4.5 D', U, A and B'=
almost not reproduced
~ 1.0 4.5 B', U, D'~almost no-t
reproduced
~ 2.0 5 not reproduced
- 29 ~
~7~7
DL-~IP~ Na 0.5 ~ CM~I 0.5 5 H'=slightly resis-tant
others-no-t reproduced
~ ~ 1.0 no-t reproduced
~ )> 2.0 5 not reproduced
None 0 ~'=30 cm r H'=20 cm,
D'=50 cm, A--75 cm,
U=10-20 cm,
B'=25 cm.
A' : koajisai (Hydrangea hirta Sieb. _ Zucc.)
B' : toneriko (Fraxinus japonica Blume)
C' : mizunara (Quercus crispula Blume)
D' : tree clethra (Clethra barbinervis Sieb. et. Zucc.)
E' : Japanese witch hazel (Hamamemis japonica Sieb. et. Zucc.)
F' : yamaurushi (Rhus trichocarpa Mig.)
G' : Japanese snowbell (Styrax japonica Sieb. et. Zucc.)
H' : nejiki (Lyonia Neziki Nakai e-t Hara)
__ _
L' : painted maple (Acer mono Maxim.)
A and L : same meanings as in Examples 2 and 4
U : torch azalia
EXAMPLE 7 :
In order to evaluate the effects o~ ~MPBs against
evergreen shrubs, sodium salt of L-AMPB, maleic hydrazide
(MH) and mixtures thereof were sprayed by foliar application
to Japanese privet (Ligustrum, japonlca Thunb., hereinafter
referred to as I'), mokkoku ( ernstroemia ja~onica Thunb. t
hereinafter referred to as J') and Japanese hawthorn ~Rha-
phiolepsis umbellata ~akino var. Mer-tensii Makino, herein-
after referred to as K') in amount of 100 litre per 10 are.
Each spraying solution contained 0.1 % of polyoxyethylene
Octylphenyletheras the surfactant.
The application and the inves-tigation were carried
out on December 14, and May 12 of -the next year respectively,
- 30 -
~7~5i7
and -the reproduction-inhibit~ncJ ef~ect was determined in
accordance with the same evaluation standard as in Example
1. The results are shown in Tables 11 and 12.
TABLE 11
Concentration (%) I' J' K'
L-AMPB Na 0.125 4 5 5
0.25 5 5 5
MH 005 1 1 1
~ 1.0 2 1.5 1.5
2.0 2.5 2 2
L-AMPB Na 0.125 + MH 0.5 5 5 5
+ 1.0 5 5 5
~ 2.0 5 5 5
L-AMPB Na 0.25 + MH 0.5 5 5 5
~ 1.0 5 5 5
+ 2.0 5 5 5
None 0 0 0
TABLE 12
Concentration (~) I' J' K'
.
DL-AMPB Na 0.25 4 5 5
0.5 5 5 5
MH 0.5 1 1 1
1.0 2 1.5 1.5
2.0 2.5 2 2
30DL-AMPB Na 0.25 + MH 0.5 5 5 5
+ i> 1.0 5 5 5
- 31 -
7~
DL~AMPB Na 0. 25 + MH 2 . O 5 5 5
DL-AM13P Na 0. 5 +MH 0. 5 5 5 5
~ ~>~ 1.0 5 5 5
+ 2.0 5 5 5
None 0 0 0
