Note: Descriptions are shown in the official language in which they were submitted.
~Q3f~491
This invention relates to a method of combating f'ungal
and bacterial in~ections of~ plants by the use of certain
triazine derivatives; and to plant anti-f'ungal and anti-
bacterial compositions, and to certain novel, specific,
triazine derivatives.
The pre~ent invention provides a proce~s for combating
fungal and bacterial diseases of plants ~Ihich compri~es
applying to plants, or to the locus of plants, a
fungicidally or hactericidally effective, but non-phy~otoxic,
amount of a triazine derivative of the general
formula:-
Rl
`f
'I /N ~ N
! R4 ~ ~
R2 R3
~' ~
Wherein Rl is alkyl, alkenyl, cycloalkyl, phenyl,
' halophenyl or adamantyl; R2 is alkyl or together with
; R3 and th~ adjacent N- atom f'orms a pyrrolidine:ring,
R3 is hydrogen, alkyl, alkoxy, phenyl or amino; and
R4 ig hydrogen or alkyl; or a salt thereof.
Preferred compounds o~ the invention for use as plant
1036~91
~ungicides and bactericides are those in which Rl
is an alkyl radical of from 1 to 6 carbon atoms or a
cycloalkyl radical; R2 is an alkyl radical oP from
1 to 4 carbon atoms; R3 is hydroge~ an alkyl radical
of from 1 to 4 carbon atoms,an alkoxy radical of from
1 to 4 carbon atoms, phenyl or amino; and R4 is hydrs~en,
or an alkyl radical of from 1 to 4 carbon atoms.
Even more preferred compounds are those wherein, in
the general formula,Rl i~ an alkyl radical of from 1 to
6 carbon àtoms,or cycloalkyl; R is an alkyl radical of
from 1 to 4 carbon atoms; R~ is hydrogen; and R is
hydroger~ or an alkyl radical of from 1 to 4 carbon
atoms.
When R is a hydrogen atom, the hydrogen is acidic,
and the compounds will form salts with bases. Examples
of such salts include alkali metal salts, for example
lithiu~, sodium and potassium salts, alkaIine earth
metal salts, for example calcium and magnesium salts,
~ ammonium salts, and salts formed from primary,
secondary3 or tertiary amines, for example primary,
secondary and tertiary aliphatic amines in which the
one, two or three aliphatic radicals each contain from
one to six carbon atoms. Salts of compounds wherein R4
represents a hydrogen atom may in general be conveniently
'
~ - 2 -
~ ~ .
.
~)364~
prepared simply by mixing the triazinedione compound
; with the stoichiometric proportions of an alkali rnetalhydroxide, alkaline earth metal hydroxide~, amm~niaJ or
amine, in a solvent or diluent. Water is generally the
most convenient solvent or diluent for this purpose.
In a further aspect the invention provides plant anti-
fungal and anti-bacterial compositions comprising as
an active ingredient a triazine derivative, or a salt
thereof, as defined in any of the preceding paragraphs;
I0 together with a carrier for the active ingredient; and,
optionally, a surface-active agent.
Particular examples of triazine derivatives useful in
the practice of the invention are set forth in Table 1
below.
TABLE 1
The compounds of Table l have the general formula:-
~
4 ~ N ~ N
R2 ,~N~ R3
- 3 -
.
.
~036~93~
~ , . _=
C~ ~ ~ o t ~ ,
~; ~ O
H ~1 ~J H t~
E~ ~ O I ~1 ~ 3
tl:l ~ O ~U GO OC) C-- r~ O CO J
~ ~ J
.
~t~ p~ X
__
~ ~ L
~ ~ rr~ ~ ~ ~ ~ ~ ~
~J N ~I X ~ ~ m ~:
X
~ _ _ _ , _
U~
~`J ~ ~ J N ~ ~ ~ ~ ~{ N
0:; C~ C) V
.
_
:~
,, 1
t
P; O ~~ S t- S '
~ o p~ o v ~ ~ ~
~ ~ 3 IS~ ~ ~1~ ~1 3 ~I 3
~ C) C~ C) O ~ X V
I N I ~1 I p~I P~ U1 I C~ I
3 C~ ~ 1 C) ~1 J~
.
_ , __ _ ~ _
~P .
O ~ 3 Ir\ ~ O~ l
~O~Oz .
_ . . ,~ _ _ .
`~
- 4-
,~
~.~)36~
æ
o
:4
o co ~ o O~ q~
~Z ~ J O O ~ J ~ ~D rd
H ~J N ~1 1~ N 1~ 1~
. I ,
_ -- ,,__, ,___ ~ ~ _
~P~ X ~ X ~ ~ X $ ~
~ _ , _~
O O p,
r~
r; ~ m
h h
:5 h h _ __ _ _~ .
r1 11~ ~ , ' O`.
~ ~ r~
O ~ r~ ~ ~ ~ ~ c~ r~ ~.
C:~ t~J ~ 5 ~ ~ N I ~C X
~S C) ~ V I
1_1
~ _
,
r-l r~ I
C-' X~ X
~ S ~ .~ ~~ S .~ u
~ C~ O t~ O ~ V
1~; I ~ I ~ ~D 3 ~ `.
~ ¦ h ¦ ~ l ¦ C) ~ X :c: X
_ , _
~ r~ ) ~\ O -1 N 1~ ~ . ~ L
,~ P-l r-l r-l r-l r~ I r~l t~
~:
00
~Z
~ l
-5- ~
1036~91
_ . . .. _ .~,
H ~
H ~ l N ,_~ O r
~:1 o~ O ~ ~O t~l O
r l U:~ ~ rJ O tU r,~ N
!~ ~ N ~-1 N N N N ~~ l ~I N
:, _ _ ,_ _
r~ rt~ r~
3~ r ~ X ~ r r.
. ~ _ _
r~
r~ r~
r~ 5 sr ~ O P, ~ C ,
~ _ ~\z
C ~ . Ir~ ~ U~
H ~ ~ ~j~ ~,r. r~J ~ ~~r~ ~ ,~ ~ ~N ,;~ ~ X
~3
~ _ _ I
E~ ~
~ d ~d ~ cl~cll ~cl d ~cl l ~
a
Z ~o ~ ~ O
:' ~E o
C~Z _~_ _____ ~ I
~ \
--6~
i -
' .
j
1~36~9~
The above listed derivatives are all novel.
In a yet further aspect, therefore, this invention
includes the specific triazine derivatives set out in
; Table 1, herein above
The compounds of formula 1 above, in genexal terms,
may be prepared by methods described in our copendiny
Canadian application No. 211730, filed October 18, 1974.
Thus, in one method, a guanidine derivative o~ ~ormula
R~ R (II) wherein
R6 and R7 may each be a hydrogen atom or an aliphatic
radical, is reacted with a chloroformic ester ClCO2R8,
wherein R8 is a hydrocarbyl group, preferably an alkyl
group of 1 to 6 carbon atoms, for example methyl or ethyl,
or preferably with a dialkylcarbonate (R80)2CO to give an
intermediate ~III). This is then further reacted with an
isocyanate RlNCO wherein Rl has any of the meanings
hereinbefore assigned to it. The
.
.
: - 7 -
49~
reaction product so obtained cyclise3 to a triazinedione
compound, as shown in the scheme below:~
NH NH2 8 CO R8
; ~C/ ClC02R I 2
NR6R7 or ~R80)2CO ~ /
NR6R7
(III)
~R lNC o
Rl
N
NR6R7
(IV)
The conversion of (III) to (IV) may be carried out in
the presence of a catalytic amount of a tertiary amine,
preferably a trialkylamine in which each of the three
alkyl groups contains 1 to 6 carbon atoms.
.
The reaction of the chloro~ormic ester ClC02R8 with
the guanidine may be carried out in water. Alternatively
- the preparation of the ethoxycarbonyl guanidine may be
~arried out by reacting diethylcarbonate with the ~ree
guanidine base in ethanol solution. In this method the
- 8 -
~C~36491
free guanidine i8 preferably prepared in ethanol b~J
adding 1 molar proportion of ~odium ethoxide to a
guanidine salt in ethanol.
Es.~.edially preferred compounds include those numbered
3~ and 40 in Table I above.
In fungicide tests compound number 40 of ~able 1 gave
good control of Wheat Rust, Puccinia recondita at an
application rate of 50 parts per million, both in an
eradicant, and in a protectant test.
:10 Compound No. 30 of Table I gave good control at the low
application rate of 3 parts per million is a translocation
(systemic) test (that is a test in which the soil
surrounding the roots of the plants was drenched with a
solution of the compound) against the oat Rust Puccinia
hordei and against Crown Rust of oats Puccinia doronata.
Against Wheat Rust, Puccinia recondita, this compound
also gave good disease control at the low application
rate o~ 5 parts per million.
he triazine derivative~ may be used as fungicides or
bactericides alone, but are.-preferably incorporated in
a composition comprising a diluent in addition to the
triazine derivative~ and may be used for a~ricultural
~', .
: .
1036491
and herbicidal purposes. The triazine derivative~
and compositions containing them, are variously active
against a variety of fungal pathogens of plants.and
seeds including, for example, the following:s
Erysiphe ~ram is (Powdery Mildew) on barley
Puooinia recondita (Rust) on wheat
Puccinia hordei ~Rust) on oats
Pytophthora _nfestans (Late Blight) on tomatoes
Pucoinia Coronata (Brown Rust) on oats
Plasmopara viticola (Downy Mildew) on vines
Unoinula necator (Powdery Mildew) on vines
Podosphaera leucotricha (Powdery Mildew) on apples
The triazine compounds, and compositions containing .
them, are also variously active against a variety of
foliage-borne bacterial plant diseases, including for
example, the following:-
Xanthomonas oryzae - (bacterial blight of rice)
Erwinia am~lovora (fireblight of pears)
:
Pseudomonas tomato (bacterial speck of tomato)
Xanthomonas vesioatoria (bacterial spot of peppers)
Pseudomonas tabaci (wildfire of tobacco)
-- 10 --
~: '
. ~ .
,
~ ;49~
For the control of both fungal and bacterial in~ection3
of plants the rate at which the triazine compound~ o~
the invention are applied will vary, depending upon the
particular compound chosen for use, the disea~e to be
controlled and on the particular species of plant
acting as host to the disease. However, a non-phytotoxic
rate of application is neces~ary, as exemplified,
hereinafter, with specific re~erence to Example~ ll and 12.
In carrying the invention process into practical effect
the growing crops, plantæ, seeds, or soil may be treated
~ . by any of the well known and established procedures
used in agriculture and crop protection. Thus, for example,
the active compound may be applied as solids, liquids,
solutions, dispersions, emulsions and these may comprise,
1n addition to the active substance, any other adjuvant
useful for formulation purposes, or any other
biologically active substance, for example to increase
` the number of diseases combated.
Such so1id or liquid substances and formulations may be
applied, ~or example, by any conventional technique, for
example~ by dusting, or btherwise applying the solid
.substances and formulations to the surfaces of growing
crops, harvested produce, plants, seeds or soil, or to
~364~
any part, or combination of parts thereof, or, for
example, applying liquids or solutions for example,
by dippin~, spraying, mist-blowing or ~oakin~ techniques.
The invention process is therefore useful for treatin~
plants, seeds, harve3ted ~ruits, vegetables, or cut
flower~ infested with, or liable to infestation with any
of the aforementioned specific fungal or bacterial
diseases.
The term "seeds" is intended to include propagative
plant forms generally and therefore includes, for example,
cut stems3 corms, tubers, rhizomes and the like.
As previously noted the triazine compounds are preferably
used in admixture with a.solid or liquid diluent. The
I admixtures so obtained are hereinafter referred to as
compositions. Preferably the compositions comprise a
surface-active agent.
.
The solid compositions may be, for example, in the form
of dusting powders, or may take the form of granules.
Suitable solid diluents include, for example3 kaolin,
bentonite, kieselguhr, dolomite, calcium carbonate, talc,
powdered magnesia and Fuller's earth.
.
- 12 -
.
" '
1~)36~9~,
Solid compositions may also be in the form of
dispersible powders or grains comprising in addition
to the active ingredient, a wetting agent to facilitate
the dispersion of the powder or grains in liquid~.
Such powders or grains may include ~illers, su~pending
agents and the like.
,
Liquid compositions include aqueous solutlons, dispersions
and emulsions containing the active ingredient
preferably in the presence of one or more surface-active
agents. Water or organic liquids may be used to prepare
solutions, dispersions, or emulsions of the active
ingredient. The liquid compositions of the invention
may also contain one or more corrosion inhibitors for
example, lauryl isoquinolinium bromide.
Surface-active agents may be of the cationic, anionic
or non-i~nic type. Suitable agents of the cationic
type include, for example, cetyltrimethyl ammonium
bromide Suitable agents of the anionic type include,
for example, soap~, salts of aliphatic monoesters of
; 20 sulphuric acid, for example, sodium lauryl sulphate;
and salts of sulphonated aromatic compounds, for example,
dodecylbenzenesulphonate, sodium, calcium and ammonium
.
- 13 -
~3~
lignosulphonate, butylnaphthalene sulphonate, and a
mixture of the sodium salt~ of diisopropyl- and
triisopropyl-naphthalenesulphonic acid. Suitable
agents o~ the non-ionic type include, f'or example,
the condensation products of ethylene oxide with ~attlJ
alcohols ~uch as oleyl alcohol and ce~yl alcohol, or
with alkyl phenols such a~ octyl-phenol, nonylphenol
and octylcresol. Other non-ionic agents are the partial
esters derived from long chain fatty acids and hexitol
anhydrides, for example, sorbitol monolaurate, and the
; condensation products of the said partial esters with
ethylene oxide and the lecithins.
The compositions which are to be used in the form of
aqueous solutions, dispersions or emulsions are
generally supplied in the form of a concentrate containing
a high proportion of the active ingredient, the
concentrate being diluted with water before use. These
concentrates are usually required to withstana storage
for prolonged periods and after such storage to be
capable of dilution with water in order to form aqueous
preparations which remain homogenous for a sufficient
, time to enable them to be applied by conventional spray
equipment. In general concentrates may conven;ently
- 14 -
contain from 10 to 85% and preferably from 25 to 60~
by wéight of active ingredient. A particul~rly preferred
form of concentrate is an emulsifiable concentrate
compri~ing a solution of a triazine derivative, as
defined above, in an organic ~olvent containing a
aur~ace-active a~ent. When required for use, the
concentrate can readily be dispersed in water by
agitation to provide a dilute emulsion auitable ~or
sprayin~. Dilute preparations ready for use may contain
varying amounta of the active ingredient, depending
,
upon the purpose for which they are to be used; however,
dilute preparations may contain between 0.0005% and
0.1% by weight of the active ingredient.
It is to be understood that the fungicidal compositions
used in this învention may comprise, in addition to
one or more triazine derlvatives, one or more other
compounds having biological activity.
The invention is illustrated, but not limitedg by
the following Examples.
.
- 15 -
~36~9JJ
EXAMPLE 1
This example illustrates the preparation of compounds
according to the invention and as listed in Table I.
(a) Preparation Or carbamate intermediate.
N,N~dimethy~guanidine hydrochloride (123.5 g; lM)
was added to a solution of potassium hydroxide (112.2 g;
2M) in water (ca. 300 ml.). The solution was stirred
and kept at -10C to -5C by cooling while ethyl
chloroformate (108.5 g; lM) was added over a period
of 45 minutes~ A~ter addition was complete, the
solution was allowed to warm to room temperature, the
~ water was evaporated in a vacuum, and the residue was
; extracted with boiling chloroform (300ml.). Theextracts were cooled, dried, and evaporated to yield
j a yellow oily solid. Recrystallisation from a 2:1
mixture of toluene and petroleum (b.p. 40-60C) gave
the white crystalline carbamate derivative (formula III,
R8=C2H5, R6=R7=CH3) having a melting point of 73-76C.
(b) Preparation of triazinedione.
The carbamate derivative so obtained wa~ dissolved in
dry toluene (ca. lOOml. per 15 g. of carbamate)
~ - 16 -
3649~
and heated under reflux with ethyl isocyanate (1 molar
proportion) and a little dry triethylamine as catalyst
~or 16 hours. The toluene was then removed in a
vacuum and the residue recrystallised from ethanol,
giving the triazine dione as a white fibrous solid of
melting point 236~238QC.
Using the appropriate guanidine starting material and
aliphatic isocyanate the following 4-aminotriazine-
diones ~Table II below) were prepared by the above
procedure,
~0369~9~
TABLE II
N ~ O
NH
H~T~R
. _ I
Rl R MELTING POINT C
~ .. _ _
C4Hg C2H5 244
. ~Q C3H7 C2H5 228
I (} ,~ : ~ iso C3H7 3 ~ 280-282
n hexyl 2 5 21~-220
n C4Hg n C4Hg . 247-248
1, iso C3H7 iso C3H7 235-237
¦ ~ CH3 241-242
':~
EXAMPLE 2
An emulsi~iable concentrate was made up by mixing together
the ingredients set out below in the proportions stated
and stirring the mixture until all the constituents were
dissolved.
- 18 -
~(~3~9~l
Compound No. 30 of Table I 10%
Ethylene Dichloride 40%
Calcium dodecylbenzene-
sulphonate 5%
; "Lubrol" L 10%
"Aromasol" H 35%
EXAMPLE 3
,:
~; A composition in the form of grains readily dispersible
in a liquid, e.g. water, was prepared by grinding together
the first three of the in~redients listed belowt in the
presence of added water and then mixing in the sodium
acetate. The resultant mixture was dried and passed
through a British Standard mesh sieve, size 44-100, to
.
obtain the desired size of grains.
Compound No. 40 (Table I) 50%
"Dispersol" T 25%
"Lubrol" AP~ 5 1.5%
Sodium Acetate 23.5%
EXAMPLE 4
'
- The ingredients listed below were all ground to~ether
in the proportions stated to produce a powder formulation
-- 19 -
~Q360~
~ readily dispersible in liquids.
: Compound No. 30 (Table I) 45%
"Di~per~ol" T 5~
"Lissapol" NX 0.5%
"Cellofas" B600 2%
Sodium acetate 47.5%
EXAMPLE 5
,
The active ingredient (Compound No. 40 of Table I) was
dissolved in a solvent and the resultant liquid was
~prayed on to the granules of Fuller's earth. The solvent
wa~ then allowed to evaporate to produce a granular
I0 composition.
Compound No. 40 (Table I) 5%
Fuller~s earth or
China clay granules 95%
EXAMPLE 6
A dusting powder was prepared by mixing, in the
proporkions stated, the active ingredient with kalc.
"
Compound No. 30 (Table I) 5%
Talc 95%
,
~o -- .
~V3649~
EXAMPLE 7
A Col formulation was prepared by ball-milling the
constituents set out below and then ~ormin~ an aqueous
~uspension of the ground mixture with water.
Compound No. 40 ~able I) 40%
"Disper~oll' 10%
"Lubrol" 1%
Water 49%
: ' .
EXAMPLE 8
1. A dispersible powder formula~ion was made by miXing
to~ether the ingredients set out below and then grinding
the mixture until all the constituents were thoroughly
mixed.
Compound No. 30 o~ Table I 25%
; ~ "Aerosol" OT/B 2%
"Dispersol" A.c. 5%
China Clay 28%
Silica 40%
- 21 -
.
~03649~
EXAMPLE 9
This example illustrate~ the preparation of two
dispersible powder ~ormulations. In ea¢h in~tan¢e all
the ingredients are mixed in the proportions ~tated and
the mixture then ground in a comminution mill.
Compound No. 40 of Table I 25%
"PERMINAL" BX 1%
"Di~persol" ~ 5%
PoIyvinyl~rrolidonë 10%
Silica 25%
China Clay 34%
., .
~` Exactly the same formulation was made using Compound
No 30. of Table I.
.
EXAMPLE 10
The ingredients set out below were formulated into a
disper3ible powder by mixing and grindin~ the ingredients
in the proportions stated.
'
Compound No. 40 of Table 25%
"AEROSOL" OT~ 2%
"Dispersol" A 5%
China Clay 68%
- 22 -
-
~03649~
Exactly the same formulation was prepared u~ing
Compound No. 30 of Table I instead o~ Compound No. 40
In Examples 2-10 above percentage amounts are on a
weight basis.
,
; 5 The following constitutes an explanation o~ the composition~
or ~ubstancefi represented by the various Trade Marks and
Trade ~ames referred to in the foregoing Examples.
"LUBROL" L is a condensate of 1 mole of nonyl
phenol with 13 molar proportions of
ethylene oxide.
"AROMASOL" H is a solvent mixture of alkylbenzenes
"DISPERSOL" T AND is a mixture of sodium sulphate and a
~ AC condensate of formaldehyde with the
i sodium salt of naphthalene sulphonic
acid.
"LUBROL" APN 5 is a condensate of 1 mole of nonyl phenol
with 5~ moles of naphthalene oxide.
"CELLOFAS" B 600 is a sodium carboxymethyl cellulose
thickener.
"LISSAPOL" NX is a condensate of 1 mole of nonyl phenol
with 8 moles of ethylene oxide.
"AEROæOL OT/B is dioctyl sodium sulphosuccinate.
"PERMINAL" ~X is an alkyl naphthalene sulphonate
(sodium salt)
.
EXAMPLE 11
The triazine derivatives were tested against a wide
- 23 - ~
,' ' ' ' ' " "
49~
variety of foliar ~ungal diseases of plant~. In the
test, a composition comprising an aqueous solution or
suspension of the test compound was sprayed on to the
foliage Or uninfected plants; the soil in whi¢h the
planta were growing was also drenched with the ¢ompo~ition.
The compositions used for spraying and drenching contained
100 parts per million (ppm.) (unless otherwlse expres~ly
stated) of the test compound. After spraying and
drenching, the plants were then exposed to infection with
the di~ aaes it was desired to control, along with
control plants not treated with the compound. After a
' period of days, depending upon the particular disease,
; the extent of the disease was visually assessedg as a
percentage of the disease established upon the control
plants which had not been treated with the compound
under test, according to the grading scheme below.
''
Gradin~Amount of disease as a percentage
of disease on contr_l plants _
0 61 to 100
l 26 to 60
' 2 6 to 25
3 O to 5
4 No disease
- 24 -
:~
~(~36491
In Table III and Table V below the names Or the diseaaes
aregiven in the rirst column, and in the second column
is given the time which elapsed between expo~ing the
plants to infe¢tion and assessing the amoun~ of di~ease.
Tables IV and VI give the te~t results.
TABLE III
_
_ TIME INTERVAL DISEASE CODE
DISEASE AND PLANT (DAYS) LE~T~R (TABLE IV)
_
PLASMOPA~A VITICOLA 7 . A
(Vine) . .
UNCINULA NECATOR 10 B
(Vine)
PODOSPHAERA LEUCOTRICHA
_ __ 10 , C
(Apple) . i _ .
',' ' '
- 2~ -
.
.
TABLE IV 1~36~9~
. .
COMPOUND NO. DISEASE CODE LE~TER
(Table I) A B C
~P 1~l3
9 3 P . 3
: 10 3 P P
O 1 3 1 ~
22o O 33 43
. 22 : O 4 4
34 4 3 P .
O 4 3
: ~ ~ ~ 3 ~ ~
"P" denotes too much phytotoxicity to get a meaningful
a~sessment of anti-fungal activity
"-" denotes not te~ted.
- 26 -
V36~
TABLE V
_ _ , l
. DISEASE AND PLANT TIME INTERVAL LETTER (TABLE ~I)
_
_ _ _ ,
Puccinia
recondita 10 D
(-heat)
ERYSIPHE GRAMINIS 10 E
(Barley)
-- ~
,
.
,
.
. - 27 - .
,
~36~g~ /
TABLE VI
COMPOUND NO. DISEASE CODE LETTERS
_
(TABLE I) D E
; APPLICATION RATE APPLICATION RATE
. . OF 100 ppm OF lOO ppm
. 3 ~ ~
4 3 O -
22 O . 3 .
9 . : APPLICATION RATE
: 10 3 1
3 P 43
. 15 3 . 1 .
6 o3 4
18 3 ~ . O
O 4
21 O 3
23 O . 4
24 ~ 4
3 2
27 3 2
~, . _
~ 28 -
1~)36~9~
.TABLE_VI Continued
. _.
' COMPOUND NO. DISEASE CODE LETTERS
~ I
(TABLE I) D E
APPLICATION RATE APPLICATION RA~E
OF 100 ppm 0~ 50 ppm
_ _ .
~ 27 3 2
: 28 3 4
29 2
3324 . 33 .
37 3
38 1 3
: RESULTS BELOW ARE AT
. . AN APPLICATION RATE
3 3 OF 25 ppm
. 7 O 2
11 1 1
12 O 4
19 4 1
. O 4
33 3 4
1 4
36 O 4
_ . _._ .
~ - 29 - .
.
1036~9~
TABLE VI Continued
. . , _ _ _
. COMPOUND NO. DISEASE CODE LETTERS
,1
tTABLE I) D E
_. _ ~
APPLICATION RATE APPLICATION RATE
OF 100 ppm 0~ lO ppm
'L, ~ _ 1 3 ~ 4
EXAMPLE 12
'
The triazine oo~pound~ were tested against a variety of
~oliage-borne bacterial plant diseases in the glasshouse.
The anti-bacterial screening method employed a mist
propagator to aid infection of treated p~ants by providing
conditions o~ high humidity.
, .
The plants were sprayed and/or root drenched with an
aqueous solution containing various concentrations of the
test chemical. After 48 hours they were inoculated with
the appropriate disease organism. Inoculations were
accompanied by wounding the plants, which was neceæsary
~or bacterial in~ection to take place. Immediately a~ter-
wards the plants were placed under high humidity. Agrimycin
(17% Streptomycin sulphate) at 2000 ppm and lOOO ppm. was
~, -
- ~O -
~036~9~
applied a~ a standard treatment and with water a~ a control.
After eight days, the symptoms were as~essed on a 0-4
scale given in Table VII below, wherein the extent of the
disease is given in the ~orm of a grading as ~ollows:-
.
Grading Perc ntage Amount Or Disease
0 61 - 100
1 26 - 60
2 6 - 25
3 . 0 - 5
4 No disease
and the disease code of Table VII is given below:-
Disease and Plant .Dieea~e Code
Xanthomonas oryzae A
(bacterial blight of rice)
Erwinia amylovora B
(fireblight on pears)
Pseudomonas tomato C
(baoterial speck of tomato)
:
~ .
- 31 -
~036491
TABLE VII
, _ . . . ,
RATE OF DISEASF, CODE
COMPOUND NO. APPLICATION
TABLE I (ppm) A B C
_
4 200 1 0 2 R/S
ll 200 2 0 3 Ris
200 3 0 3 R/S
18 . lOO l 3 ~ R/S
2 lOO ~ 0 3 R and S
: . ~ - 2* 3 3 R and S
;, .
R/S denote~ a combined root drench and foliar spray test.
R and S denote individual root drench and ~oliar spray
tests .
* denote~ a result obtained by a foliar spray test
alone.
.
.
:
. ~
~ -32- .
- .
