ALCOHOL ALKOXYLATES AS ADJUVANTS FOR AGROCHEMICAL
FORMULATIONS
This invention relates to bioperformance enhancing adjuvants and to use of such
..adjuv.a.nts.
Numerous adjuvants which enhance the bioperformance of agrochemicals are
5 known. A broad mention of alcohol alkoxylates as penetration aids is made in
W02008/037375.
The present invention provides a bioperformance enhancing adjuvant of formula (I):
RIO[BO]~[AO],~R. ~ (I)
where BO is butylene oxide; and each A0 is independently propylene oxide or ethylene
lo oxide; n is from 1 to 12;. m is from 0 to 20; R1 is optionally substituted C4-20 alkyl or
optionally substituted C4-2() alkenyl; and R2 is hydrogen or optionally substituted
CI-4 alkyl; provided that R1 comprises more carbon atoms than R2.
Each alkyl chain is, independently, straight or branched.
Optional substituents on the alkyl and alkenyl groups are, independently, hydroxy
15 and epoxy groups.
Certain butylene oxide-ethylene oxide block copolymers are disclosed by
J.Chlebicki in J.Colloid and Interface Science 206, 77-82 (1998).
Therefore in another aspect, the present invention provides a compound of
formula (I) as defined above provided that it is not a compound of formula (Ia):
20 R30[CH2CH(C2H5>O]a[C2H40]bH (la)
when R3 is n-butyl, n-hexyi, n-octyl or n-decyl; a is 1,2,3 or 4; and b is from 9.7 to10.2.
When R1 is optionally substituted alkyl, suitably RI is optionally substituted C6-18 alkyl;
more suitably RI is optionally substituted Cla-1a6l kyl; even more suitably R1 is optionally
substituted C13-,.ajl kyl.
25 When R1 is optionally substituted alkenyl, suitably R1 is optionally substituted
Cfj-18 alkenyl; more suitably R1 is optionally substituted oleyl; even more suitably RI is
oleyl.
Suitably R2 is hydrogen or optionally substituted CI-3a lkyl; more suitably R2 is
hydrogen or optionally substituted CISa2l kyl; even more suitably R2 is hydrogen or
30 optionally substituted methyl; most suitably R2 is hydrogen.
Suitably R1 is non-substituted alkyl.
Suitably R2 is hydrogen or non-substituted alkyl.
BO [butylene oxide] has the empirical formula C4Hs0. Every BO unit has the
formula CH(&)CH(R5)0 but each BO unit is independently selected from the following
options: Rq is methyl and Rs is methyl; or R? is ethyl and Rs is hydrogen; or Rq is
hydrogen and RS is ethyl.
P~opyleneo xide [PO] has-the empirical_formulaC 3H60. E~very-EOu nit.has the
formula CH(R6)CH(R7)0 but each PO unit is independently selected from the following
5 options: % is methyl and R7 is hydrogen; or R6 is hydrogen and R7 is methyl.
In one aspect, the block [AO], is a PO block followed by an EO block, where the
PO block is bonded to the BO block, such that the adjuvant is of formula (Ib):
RI~ [ B ~ l n [ P ~ l m ~ [ E ~(lIbm) * ~ ~ ~
where (m' + m" = m) and RI, R2, n and m are as defined for compounds of formula (I).
10 Suitably A0 is ethylene oxide.
Suitably n is from 2 to 8; more suitably from 3 to 6; even more suitably it is 4.
Suitably m is from 5 to 15; more suitably it is from 8 to 12; even more suitably it
is 10.
In one aspect, m=O. Adjuvants for which m=O may display very low levels of
15 phytotoxicity [i.e. little damage to plants].
The bioperformance enhancing adjuvants of the present invention may be used
effectively at much lower concentrations than the effective concentrations for
conventional adjuvants.
The bioperformance enhancing adjuvants of the present invention may be used
20 synergistically with other bioperformance enhancing adjuvants of the present invention
or with conventional adjuvants.
The values of n and m represent values both for individual species and for
averages taken over a distribution of compounds. This will be well understood by the
skilled person.
2 5 Suitably the bioperformance enhancing adjuvants of the present invention are
used to enhance the bioperformance 0f.a pesticide. Pesticides suitable for use with the
present invention include insecticides, fungicides, herbicides, acaricides, nematicides and
biocides suitable for controlling pests, diseases or weeds that are a problem in
agriculture. Many such pesticides are known and are described in The Pesticide Manual
30 14th edition published by the British Crop Protection Council in 2006.
The invention is illustrated by the following non-limiting Examples in which all
parts and percentages are by weight unless otherwise stated.
EXAMPLE I
This example illustrates compounds of the present invention. Twenty eight
butylene oxide based compounds were synthesised using standard techniques familiar to
. a-skilled person. [for.example,-see. EF!068.1865A]. -Each. sample-consists-of. a.hydrocarbon.-.
tail connected to a butyIene oxide section which in turn is connected to an ethylene oxide
5 section; the samples are compounds of formula (I) in which A0 is ethylene oxide and R2
is hydrogen; and R1, n and m are as defined in Table 1. Samples 1 to 3 and 24 to 27
were prepared using branched alcohols containing an average of 13 carbon atoms.
Samples 4 to 7 were prepared with 2-ethylhexyl alcohol. Samples 8 to 11 were prepared
using butanol as the starting solvent. Samples 12 to 14 and sample 28 used a fraction of
lo alcohols ranging from 12 to 15 carbons in length. Samples 15 to 23 used an alcohol
range from C12 to C16. The values of n and m are average values.
Table 1
Sample R1 alkyl chain
1 C 1 [average]
2 C 13 [average]
3 C 1 [average]
4 2-ethylhexyl
5 2-ethylhexyl
6 2-ethylhexyl
7 2-ethylhexyl
8 c4
9 c4
10 c4
11 c4
12.. . .
c12-15 '' .
13 c12-15
14 c12-15
15 c12-16
16 c12-16
17 c12-16
18 c12-16
19 c12-16
c12-16
c12-16
-C12-16 . --
c12-16
C13 [average]
C 13 [average]
C l3 [average]
C l3 [average]
c12-15
C18 (oley]?
c 18 (oleyl)
EXAMPLE 2
This example shows that samples 15, 17,24 and 25 from Table 1 behave as adjuvants for
hgicides used against brown rust (puccinia recondita). Wheat was grown outside in
5 field plots. Each plot was sprayed with water at a rate of 15 litres per hectare, the water
containing either difenoconazole or cyproconazole, at a concentration which enabled a
pesticide application rate of 0.1, I, 3, 10 or 30 grams per hectare. Adjuvants were
added at the standard rate of 0.2% vlv of the spray volume used. The known adjuvants
~ r i96j an~d T~EHP (tris 2-ethylhexyl phosphate) were also tested for comparison. Each
10 experiment was replicated four times and the results were averaged at each rate. Plants
were examined for both protective action and curative effects. A standard mathematical
analytical technique was used: Plots of efficacy against pesticide concentration for each
adjuvant were 'logit' transformed and used to estimate the concentration required for
90% effect (ED90). For each sample, its ED90 value was compared to that of the known
I 5 adjuvant BrijTM96 or TEHP in order to generate a relative potency; the-relative potency is
the ratio of the ED90 values. Relative potencies are given in Table 2 [relative potency
results compared to BrijTM96 for difenoconazole] and Table 3 [relative potency results
compared to TEHP for cyproconazole]. Adjuvants which performed better than the
standard adjuvants have a relative potency value greater than 1.
Table 2
Sample Protective Curative
Table 3
Sample Protective Curative
15 1.80 3.81
17 0.97 2.73
24 1.68 2.97
2 5 1.22 4.29
EXAMPLE 3
5 In this example Sample 13 from Table 1 was compared to the oil adjuvant blend
~ u r b o c h a r ~ Teh~e~ h.e rbicide fomesafen was applied to the weed species xanthium
strumariurn (XANST), setaria viridis (SETVI), abutilon theophrasti (ABUTH), and
chenopodium album (CHEAL) at rates of 60 or 120 grams per hectare, using a laboratory
track sprayer. Each experiment was replicated four times and the percentage damage to
10 the weeds was assessed visually at time periods of 7, 14 and 21 days after application.
Each adjuvant was applied at a rate of 0.5% of the volume of the spray water. Four
effects were evaluated: pesticide rate (2 levels), adjuvant type (two levels), weed species
(four levels) and days after application (three levels). A standard simple linear model
was constructed to judge the significance of these effects. These effects were found to be
15 significant at a 5% level. A model was fitted using multiple linear regression using the
statistics package JMP (SAS group). The effect of each adjuvant was pulled out from the
model and the least significant differences evaluated using a Student's t method. In
further examples, where a greater number than two adjuvants were compared, Tukey's
IISD method was used.
2 0
Table 4 shows the mean efficacy of the butylene oxide adjuvant number 13 with the
pesticide fomesafen compared to the oil adjuvant Turbocharge across four weed species
and compared to single weed species. The mean values and a letter code denoting
significant difference (samples with the same letter are not significantly different from
each other at the 5% level.) I11 addition the mean values split according to individual
weed species are also shown. As can be seen, Sample 13 was more efficacious than the
standard adjuvant..~urbochar~~~~..acrowssee.tdh sep ecies, andwasas good or..betteron . . ...
individual weeds.
5 Table 4
Sample Allweeds XANST CHEAL SETVI ABUTH
Sample 13 61.8; A 89.7; A 89.4; A 27.5; A 40.55; A
Turbocharge 58.8; B 83.9; B 88.6; A 24.4; B 38.33; A
EXAMPLE 4
In this example Sample 13 from Table 1 was compared to the adjuvant
~ r i j ~ ~T9he6 h~erb.ic ide fomesafen was applied to the weed species xanthium
10 strumarium (XANST), setaria viridis (SETVI), abutilon theophrasti (ABUTH), and
chenopodium album (CHEAL) at rates of 60 or 120 grams per hectare by a laboratory
track sprayer. Each experiment was replicated four times and the percentage damage to
the weeds was assessed visually at time periods of 7, 14 and 2 1 days after application.
Each adjuvant was applied at a rate of 0.2% of the volume of the spray water.
15 The same statistical methodology that was applied in Example 3 was used here.
Table 5 shows the mean efficacy of the butylene oxide adjuvant number 13 with
the pesticide fornesafen compared to the adjuvant Brij 96 across four weed species and
compared to single weed species. The mean values and a letter denoting which group
each adjuvant belonged to are shown. In addition the mean values split according to
20 individual weed species are also shown. As can be seen the butylene oxide adjuvant was
more efficacious than the standard adjuvant across the weed species, and was as good or
better on individual weeds.
Table 5
Sample All weeds ABUTH CHEAL SETVI XANST
Brij 96V 53.33; B 32.2; A 82.5; A 26.66; A 71.94; B
EXAMPLE 5
In this example the rate response of the butylene oxide adjuvant number 13 of Table 1
5 was measured to display the excellent performance of this adjuvant at very low rates.
compared to the adjuvant ~ r i j ? ' ~ 9 T6h~e. h erbicide fomesafen was applied to the weed
species xanthium strumarium (XANST), setaria viridis (SETVI), abutilon theophrasti
(ABUTH), and chenopodium album (CHEAL) at rates of 60 or 120 grams per hectare by
a laboratory track sprayer. Each experiment was replicated four times and the percentage
lo damage to the weeds was assessed visually at time periods of 7, 14 and 21 days after
application. The adjuvants were each applied at a rate of 0.2% of the volume of the spray
water.
The same statistical methodology that was applied in Example 3 was used here. Where a
15 sample has more than one letter it is not significantly different to any other sample with
one of those letters.
Table 6 shows the mean efficacy of the butylene oxide adjuvant Sample 13 at several
addition rates with the pesticide fomesafen compared to the adjuvant Brij 96V across
20 four weed species, the mean values and a letter denoting which group each adjuvant
belonged to are shown. As can be seen the butylene oxide adjuvant was more efficacious
than the standard adjuvant across the weed species. In addition it was as effective at half
the rate of the standard Brij96V (Sample 13 at O:l% cf.-Brij 96V at 0;2%).-- T-he-level of
addition of the butylene oxide adjuvant that was statistically better than no adjuvant was
25 0.025%. This is a very low level of adjuvant addition, indicating the remarkable efficacy
of this adjuvant.
Table 6
Sample Adjuvant rate (%) Rank Mean % kill
Sample 13 0.5 A -61.805
Sample 13 0.2 B 57.15
Sample 13 0.1 RC 54.23
Brij 96 0.2 C 53.33
Sample 13 0.05 D 43.95
Sample 13 0.025 E 38.12
No adjuvant 0 F 27.57
EXAMPLE 6
In this example the butylene oxide adjuvant Sample 13 of Table 1 was compared
5 to the adjuvant ween^^ 20. The herbicide mesotrione was applied at rates of 45 and 90
grams per hectare by a laboratory track sprayer to the weed species brachiaria platyphyla
(BRAPL), digitaria sanguinalis (DIGSA), polygonum convolvulus (POLCO) and
amaranthus tuberculatus (AMATU). In each case the experiments were replicated four
times and the percentage damage to the weeds was assessed visually at time periods of 7,
10 14 and 21 days after application. The adjuvants was applied at a rate of 0.5% of the
volume of the spray water.
The same statistical methodology that was applied in Exanlple 3 was used here.
Table 7 shows the mean efficacy of the butylene oxide adjuvant Sample 13 at a
rate of 0.5 % vlv with the pesticide mesotrione compared to the adjuvant Tween 20
15 across four weed species and compared to single weed species. The mean values and a
letter denoting which group each adjuvant belonged to are shown. In addition the mean
values split according to individual weed species are also shown. As can be seen the
butylene oxide adjuvant was more efficacious than the standard adjuvant across the weed
species, and was as good or better on individual weeds.
20 Table 7
Sample All weeds BRAPL DIGSA POLCO AMATU
Sample 13 69.986; A 54.72; A 56.94; A 97.167; A 7 1.1 1 ; A
Tween 20 63.861; B 44.72; B 48.33; B 95.44;A 66.94; AB
No adjuvant 44.986; C 20.27; C 19.44; C 77.16; B 63.05; B
EXAMPLE 7
In this example the butylene oxide adjuvant Sample 13 of Table1 was compared
to-the adjuvant.~rij??~96T~he. herbicidemesotrionewas.applied to the-weed speciesbrachiaria
platyphyla (BRAPL), digitaria sanguinalis (DIGSA), polygonum convolvulus
5 (POLCO) and amaranthus tuberculatus (AMATU) at rates of 45 or 90 grams per hectare
by a laboratory track sprayer. Each experiment was replicated four times and the
percentage damage to the weeds was assessed visually at time periods of 7, 14 and 21
days after application. The adjuvants were applied at a rate of 0.2% of the volume of the
spray water.
10 The same statistical methodology that was applied in Example 3 was used here.
Table 8 shows the mean efficacy of the butylene oxide adjuvant Sample 13 at a
rate of 0.2% v/v with the pesticide mesotrione compared to the adjuvant Brij 96V across
four weed species, and compared to single weed species. The mean values and a letter
denoting which group each adjuvant belonged to are shown. In addition the mean values
I5 split according to individual weed species are also shown. As can be seen the butylene
oxide adjuvant was more efficacious than the standard adjuvant across the weed species,
and was as good or better on individual weeds.
Table 8
Sample All weeds BRAPL DIGSA YOLCO AMATU
Sample 13 68.44; A 5 1.66; A 54.72; A 97.1 1; A 70.28; A
Brij 96V 61.4; B 41.94; B 44.72; B 93.66; B 65.28; B
No adjuvant 44.99; C 20.27; C 19.44; C 77.16; C 63.05; B
20
EXAMPLE 8
In this example the rate response of the butylene oxide adjuvant-Sample I3 of- -
Table 1 was measured to display the excellent performance of this adjuvant at very low
rates compared to the adjuvant ~ r i j ' ~ 9 6T~h.e herbicide mesotrione was applied to the
25 weed species brachiaria platyphyla (BRAPL), digitaria sanguinalis (DIGSA), polygonum
convolvulus (POLCO) and amaranthus tuberculatus (AMATU) at rates of 45 or 90 grams
per hectare by a laboratory track sprayer. Each experiment was replicated four times and
the percentage damage to the weeds was assessed visually at time periods of 7, 14 and 21
days after application. The butylene oxide adjuvant was applied at rates of 0.025, 0.05,
0.1, 0.2 and 0.5% wlv of the spray water. For comparison Brij96V was added at a rate of
0.2% wlv.
.The.same..statistical. methodology .that-was .applied in Example..3-was..used-here..
Table 9 shows the mean efficacy of the butylene oxide adjuvant Sample 13 at
5 several addition rates with the pesticide mesotrione compared to the adjuvant Brij 96V
across four weed species. The mean values and a letter denoting which group each
adjuvant belonged to are shown. As can be seen half the rate of the butylene oxide
adjuvant was more efficacious than the standard adjuvant (0.1 % vs 0.2 %). In addition it
was as effective at one quarter of the rate of the standard Brij96V (0.05 % vs 0.2%).
10 The level of addition of the butylene oxide adjuvant that was statistically better than no
adjuvant was 0.025 %. This is a very low level of adjuvant addition indicating the
remarkable efficacy of this adjuvant.
Table 9
Sample
Sample 13
Sample 13
Sample 13
Sample 13
Brij 96
Sample 13
No adjuvant
Adjuvant rate % Rank Mean % kill Standard error
EXAMPLE 9
In this example the rate response of the butylene oxide adjuvant Sample 13 of
Table I was measured to display the excellent performance of this adjuvant at very low
rates. The herbicide pinoxaden was applied to the weed species lolium perenne
(LOLPE), alopecurius myosuirides (ALOMY), setaria viridis (SETVI) and avena fatua
20 (AVEFA) at rates of 7.5 or 15 grams per hectare by a laboratory track sprayer. Each
experiment was replicated four times and the percentage damage to the weeds was
assessed visually at time periods of 14 and 21 days after application. The butylene oxide
adjuvant was applied at rates of 0.025,0.05, 0.1, 0.2 and 0.5% wlv of the spray water.
'l'he same statistical methodology that was applied in Example 3 was used here.
Table 10 shows the mean efficacy of the butylene oxide adjuvant Sample 13 at
several addition rates with the pesticide pinoxaden. Results are meaned across four weed
-. -. . .. species.-The_mean.yalues.anda.. letter..denoting..which.groupheea~h.hadjjuvanttbbe1o~~. g.- ed-. dtt~O
are shown. The results show that the butylene oxide adjuvant is efficacious at a very low
5 level (0.025%) and that there is a strong rate response to the added adjuvant.
Table 10
Sample Adjuvant rate % Rank Mean % kill Standard error
Sample 13 0.5 A 76.89 1.441
Sample 13 0.2 B 73.89
Sample 13 0.1 B 73.45
Sample 13 0.05 C 67.53
Sample 13 0.025 D 60.76
No adjuvant 0 E 4.72
EXAMPLE 10
10 In this example the butylene oxide adjuvant Sample 13 of Table 1 was compared
to the commercial oil adjuvant blend ~ t ~ i u sIF~. ~Th4e 1he rbicide nicosulfuron was
applied to the weed species chenopodium album (CHEAL), digitaria sanguinalis
(DIGSA), setaria viridis (SETVI) and abutilon theophrasti (ABUTH) at rates of 30 or 60
grams per hectare by a laboratory track sprayer. Each experiment was replicated four
15 times and the percentage damage to the weeds was assessed visually at time periods of 14
and 21 days after application. The adjuvants were applied at a rate of 0.5% of the
volume of the spray water.
The same statistical methodology that was applied in Example 3 was used here.
Table 1 1 shows the mean efficacy of the-butylene oxide adjuvant Sample 13 at a
20 rate of 0.5%v/v with the pesticide nicosulfuron compared to the oil adjuvant
~ t ~ l u s ~F~ ac4ro1ss1 fo ur weed species and compared to single weed species. The mean
values and a letter denoting which group each adjuvant belonged to are shown. In
addition the mean values split according to individual weed species are also shown. As
can be seen the butylene oxide adjuvant was more efficacious than the standard adjuvant
25 across the weed species, and was as good or better on individual weeds.
Table 11
Sample All weeds ' CHEAL SETVI DIGSA ABUTH
Sample 13 76.15; A 84.58; A 90; A 81.25; A 48.75; A
Atplus.4.1.1J &j4r/.5;..B.. 74..1.7;.-B.- -8 1..58;..B. -.78.-75;-A..- 32,5;-.B.-
No adjuvant 20.94; C 12.08; C 41.67; C 8.75; B 21.25; C
EXAMPLE 1 1
In this example the butylene oxide adjuvant Sample 13 of Table 1 was compared to
the commercial adjuvant tris 2-ethylhexyl phosphate (TEHP). The herbicide
5 nicosulfuron was applied to the weed species chenopodium album (CHEAL), digitaria
sanguinalis (DIGSA), setaria viridis (SETVI) and abutilon theophrasti (ABUTH)at rates
of 30 or 60 grams per hectare by a laboratory track sprayer. Each experiment was
replicated four times and the percentage damage to the weeds was assessed visually at
time periods of 14 and 21 days after application. The adjuvants were applied at a rate of
10 0.2% of the volume of the spray water.
The same statistical methodology that was applied in Example 3 was used here.
Table 12 shows the mean efficacy of the butylene oxide adjuvant Sample 13 at a
rate of 0.2% v/v with the pesticide nicosulfuron compared to the adjuvant TEHP the
same rate across four weed species, and compared to single weed species. The mean
15 values and a letter denoting which group each adjuvant belonged to are shown along with
the standard error. In addition the mean values split according to individual weed species
are also shown. As can be seen the butylene oxide adjuvant was more efficacious than
the standard adjuvant across the weed species, and was as good or better on individual
weeds.
20 Table 12
Sample Allweeds CHEAL SETVI DIGSA ABUTH
Sample 13 68.23;A 76.67;A 80; A 73.33; A 42.92; A
TEHP 58.12; B 68.33; B 77.08; A 69.17; A 17.92; B
No adjuvant 20.94; C 12.08; C 41.67; B 8.75; B 21.25; B
EXAMPLE 12
In this example the rate response of the butylene oxide adjuvant Sample 13 of
-Table 1 wasmeasured and compared to the adjuvant TEHP, The herbicide nicosufurpn
was applied to the weed species chenopodium album (CHEAL), digitaria sanguinalis
5 (DIGSA), setaria viridis (SETVI) and abutilon theophrasti (ABUTH) at rates of 30 to 60
grams per hectare by a laboratory track sprayer. Each experiment was replicated four
times and the percentage damage to the weeds was assessed visually at time periods of 14
and 21 days after application. The butylene oxide adjuvant was applied at rates of 0.025,
0.05,0.l, 0.2 and 0.5% w/v of the spray water. For comparison TEHP was added at a
10 rate of 0.2% wlv.
The same statistical methodology that was applied in Example 3 was used here.
Table 13 shows the mean efficacy of the butyle~leo xide adjuvant Sample 13 at
several addition rates with the pesticide nicosulfuron. Results are meaned across four
weed species. As a comparison the adjuvant TEHP was added at 0.2% v/v. The mean
15 values and a letter denoting which group each adjuvant belonged to are shown. As can
be seen half the rate of the butylene oxide adjuvant was more efficacious than the
standard adjuvant (Sample 1 3 at 0.1 % compared to TEHP at 0.2%). In addition it was as
effective at one quarter of the rate of the standard TEHP (0.05% compared to 0.2%).
The level of addition of the butylene oxide adjuvant that was statistically better than no
20 adjuvant was 0.025%. This is a very low level of adjuvant addition, indicating the
remarkable efficacy of this adjuvant.
Table 13
Sample Adjuvant rate % Rank Mean % kill Standard error
-- .-.
Sample 13 0.5 A 76.14 1 .SO3
Sample 13 0.2 B 68.23
Sample 13 0.1 C 63.23
TEHP 0.2 D 58.12
Sample 13 0.05 D 56.35
Sample 13 0.025 E 51.87
No adjuvant 0 F 20.93
EXAMPLE 13
In this example the responses of the butylene oxide adjuvants 13, 17, 19,2 I, 22
_and 23 of Table 1-were measured at an application rate-of-0.2% of-the volume of-the
spray solution used. They were compared to the commercial tank mix adjuvant
5 ~ t ~ l u s l 'I~F4, w1h ich was applied at the recommended rate of 0.5% by volume. The
herbicide nicosufuron was applied to the weed species chenopodium album (CHEAL),
digitaria sanguinalis (DIGSA), setaria viridis (SETVI) and abutilon theophrasti
(ABUTH) at rates of 30 or 60 grams per hectare by a laboratory track sprayer. Each
experiment was replicated four times and the percentage damage to the weeds was
10 assessed visually at time periods of 14 and 21 days after application.
The same statistical methodology that was applied in Example 3 was used here.
Table 14 shows the mean efficacy of six butylene oxide adjuvants at an addition
rate of 0.2% with the pesticide nicosulfuron. Results are meaned across two pesticide
rates and each sample was replicated four times. As a comparison the adjuvant
1s 41 IF was added at 0.5% vlv. The mean values and a letter denoting which group each
adjuvant belonged to are shown. The data shows that the butylene oxide adjuvants were
at least as good as the standard which was used at a higher rate than the butylene oxide
adjuvants (0.2% compared to 0.5%).
Table 14
Sample
Sample 13-
Sample 2 1
Sample 22
Sample 19
Sample 23
Sample 17
No adjuvant
All weeds
78.44; A
ABUTH
65.42; A
66.25; A
61.67; A
65; A
62.92; A
60.83;- A
58.75; A
25.83; B
CHEAL
85; A
85; A,
85.83; A
84.17; A
82.08; A
74:17; B -
76.67; B
24.16; C
DIGSA SETVI
EXAMPLE 14
In this example the responses of the adjuvants 13, 17, 19,2 I, 22 and 23 were
measured at an application rate of 0.2% of the volume of the spray solution used. They
were cornpared to the adjuvant tris 2-ethylhexyl phosphate (TEHP), which was applied at
25 the rate of 0.5% by volume. ?'he herbicide pinoxaden was applied at rates of 7.5 or 15
grains per hectare by a laboratory track sprayer to the weed species lolium perenne
(LOLPE), alopecurius myosuirides (ALOMY), setaria viridis (SETVI) and avena fatua
(AVEFA).-.In.each case-the-experiments were-replicated-fourtimes-and-the-percentagedamage
to the weeds was assessed visually at time periods of 14 and 21 days after
5 application.
The same statistical methodology that was applied in Example 3 was used here.
Table 15 shows the mean efficacy of six butylene oxide adjuvants at an addition
rate of 0.2% with the pesticide pinoxaden. Results are meaned across two pesticide rates
and each sample was replicated.four times. As a comparison the adjuvant tris 2
10 ethylhexyl phosphate was added at 0.5% v/v. The mean values and a letter denoting
which group each adjuvant belonged to are shown along with the standard error. The
standard TEHP was used at a higher rate than the butylene oxide adjuvants (0.2%
compared to 0.5%).
Table 15
Sample A11 weeds SETVI LOLPE AVEFA ALOMY
Sample 23 76.98; A 78.75; ABC 78.33; AB 78.33; AB 72.5; A
Sample 13 76.98; A 83.33; A 77.5; AB 80.42; A 66.67; B
Sample19 76.25;A 80; AB 77.08; AB 77.08; AB 70.83; AB
TEHP 75.63; A 77.5; ABC 82.5; A 73.75; AB 68.75; AB
Sample 22 73.96; AB 78.33; ABC 72.5; BC 75.83; AB 69.17; AB
Sample 21 72.19; AB 7 1.25; C 76.67; AB 7 1.66; B 69.1 7; AB
Sample 17 68.02; B 72.92; RC 68.75; C 73.33; AB 57.08; C
No adjuvant 1 5.62; C 17.08; D 7.08; D 23.33; C 15; D
15
EXAMPLE 15
In this example the rate response of the butylene oxide sample 27 of-Table -1 was
measured, displaying the excellent performance of this adjuvant compared to the
commercial adjuvant ~ u r b o c h a r ~uese~d ~at, a rate of 0.5% by volume. The herbicide
20 fomesafen was applied to the weed species xanthium strumarium (XANST), setaria
viridis (SETVI), abutilon theophrasti (ABUTH) , and chenopodium album (CHEAL)at
rates of 60 or 120 grams per hectare by a laboratory track sprayer. Each experiment was
replicated four times and the percentage damage to the weeds was assessed visually at
time periods of 7, 14 and 21 days after application. Sample 27 was applied at a rate of
25 0.2% of the volume of the spray water.
The same statistical methodology that was applied in Example 3 was used here
Table 16 shows the mean efficacy of the butylene oxide adjuvant 27 at a rate of 0.2% v/v
_with-thep. esticide-fon~esafenc.o mpared .to .the-adjuvant..Turbocharge-at-a-rate0-.5oYfo ..
The mean values and a letter denoting which group each adjuvant belonged to are shown
5 along with the standard error. As can be seen the butylene oxide adjuvant was as
effective as Turbocharge even although it was applied at 0.2% as opposed to 0.5% for the
commercial adjuvant.
Table 16
Sample A11 weeds XANST SETVI CHEAL ABUTH
Sample 27 51.01; A 73.44; A 33.44; A 74.3; A 22.86; B
Turbocharge 52.89; A 72.33; A 28.72; B 75.69; A 34.81; A
No adjuvant 22.94; B 31.55; B 13.78; C 30.69; B 15.75; C
EXAMPLE 16
In this example the rate response of the butylene oxide adjuvant 27 of Table 1
was measured to display the excellent performance of this adjuvant compared to the
commercial adjuvant TweenTM20, used at a rate of 0.5% by volume. The herbicide
mesotrione was applied to the weed species brachiaria platyphyla (BRAPL), digitaria
15 sanguinalis (DIGSA), polygonurn convolvulus (POLCO) and amaranthus tuberculatus
(AMATU) at rates of 45 or 90 grams per hectare by a laboratory track sprayer. Each
experiment was replicated four times and the percentage damage to the weeds was
assessed visually at time periods of 7, 14 and 21 days after application. Sample 27 was
applied at a rate of 0.2% of the volume of the spray water.
20 The same statistical methodology that was applied in Example 3 was used here.
Table 17 shows the mean efficacy of the butylene oxide adjuvant 27 at a rate of
- 0.2% vlv with the pesticide mesotrione compared to the adjuvant Tween 20 at a rate of
0.5%. The mean values and a letter denoting which group each adjuvant belonged to are
shown. As can be seen the butylene oxide adjuvant was as effective as Tween 20 even
25 although it was applied at 0.2% as opposed to 0.5% for the commercial adjuvant.
Table 17
Sample Allweeds POLCO DIGSA BRAPL AMATU
----- . --- - --Sample 27-. - 57.26; A 75.44; A -44.99; A 36.94; A 71.64; A ---- - - - -
Tween 20 54.54; A 73.61; A 41.67; A 33.06; B 69.86; A
No adjuvant 34.84; B 55.5; B 20.55; B 19.17; C 44.13; B
EXAMPLE 17
In this example the response of butylene oxide sample 27 of Table 1 was
5 measured at an application rate of 0.2% of the volume of the spray solution used. It was
compared to the adjuvant ~ e n o ~ o l " ~ ~w0h8ic0h ,w as also applied at a rate of 0.2% by
volume. This adjuvant has the same alkyl chain and ethylene oxide head group as
Sample 27 however it does not contain the butylene oxide moiety. The herbicide
pinoxaden was applied at rates of 7.5 or 15 grams per hectare by a laboratory track
10 sprayer to the weed species lolium perenne (LOLPE), alopecurius myosuirides
(ALOMY), setaria viridis (SETVI) and avena fatua (AVEFA). Each experiment was
replicated four times and the percentage damage to the weeds was assessed visually at
time periods of 14 and 2 1 days after application.
The same statistical methodology that was applied in Example 3 was used here.
15 Table 18 shows the mean efficacy of the butylene oxide adjuvant 27 at a rate of
0.2% v/v with the pesticide pinoxaden compared to the adjuvant Genapol X080 at the
same rate. The mean values and a letter denoting which group each adjuvant belonged to
are shown. The data shows that the butylene oxide adjuvants was significantly more
efficacious than Genapol X08O across the range of weed species tested.
Table 18
Sample All weeds SETVI- - - LOLPE AVEFA - ALOMY
Sample 27 71.06; A 84.4; A 59.22; A 82.3; A 58.3 1; A
Genopol X080 52.08; B 70.67; B 20.97; B 75.47; B 41.23; B
No adjuvant 7.44; C 4.75; C 6.53; C 5.74; C 12.73; C
EXAMPLE 18
In this example the response of butylene oxide sample 27 of Table 1 was
25 measured at an appjication rate of 0.2% by volume of the spray solution used. It was
compared to the commercial tank mix adjuvant AtplusTM41IF , which was applied at the
recommended rate of 0.5% by volume, and to the adjuvant ~ e n a ~ o l ~w~hi~ch0 w8as0
applied-at 0.2%. _This-adjuvant has the_same_alkyl.chain and-ethylene oxide-head groupas
sample 27 however it does not contain the butylene oxide moiety. The herbicide
5 nicosufuron was applied at rates of 30 or 60 grams per hectare by a laboratory track
sprayer to the weed species chenopodium album (CHEAL), digitaria sanguinalis
(DIGSA), setaria viridis (SETVI) and abutilon theophrasti (ABUTH). In each case the
experiments were replicated four times and the percentage damage to the weeds was
assessed visually at time periods of 14 and 21 days after application.
10 The same statistical methodology that was applied in Example 3 was used here.
Table 19 shows the mean effrcacy of the butylene oxide adjuvant 27 at a rate of
0.2 % v/v with the pesticide nicosulfuron compared to the adjuvant Genapol X080 at the
same rate, and to Atplus 41 IF applied at the higher rate of 0.5%. The mean values and a
letter denoting which group each adjuvant belonged to are shown. The data shows that
15 the butylene oxide adjuvants was as good as Atplus 41 1F which was used at a higher rate
than the butylene oxide adjuvants (0.2% compared to 0.5%). It was more efficacious
than Genapol X080.
Table 19
Sample A11 weeds SETVI DIGSA CHEAL ABUTH
Sample 27 70.26; A 45.13; A 79.55; A 84.58; A 71.76; A
Atplus 41 1F 65.74; A 25.96; B 76.05; A 85.01; A 75.93; A
Genopol X080 46.47; B 19.72; C 42.71; B 70.42; B 53.01; B
No adjuvant 21.39; C 14.17; D 22.59; C 15.2; C 33.6; C
2 0 EXAMPLE 19
In this example the rate response of the butylene oxide adjuvant 13 of Table 1 -
was measured to display the excellent performance of this adjuvant compared to the
commercial adjuvant ~urbochar~e'u~se, d at a rate of 0.5% by volume. The herbicide
fomesafen was applied at rates of 60, 90 or 120 grams per hectare by a laboratory track
25 sprayer to the weed species xanthium strumarium (XANST), abutilon theophrasti
(ABUTH), and chenopodium album (CHEAL). In each case the experiments were
replicated four times and the percentage damage to the weeds was assessed visually at
time periods of 14 and 2 1 days after application. Sample 13 was applied at a rate of
0.2% of the volume of the spray water.
The same statistical methodology that was applied in Example 3 was used here.
Table 2 1 shows the mean efficacy of the butylene oxide adjuvant 13 at a rate of
0.2%.vLv-with the pesticide-fomesafen-compared to the adjuvant-Turbocharge applied at
the higher rate of 0.5%. The mean values and a letter denoting which group each
5 adjuvant belonged to are shown. As can be seen the butylene oxide adjuvant was more
effective than Turbocharge even although it was applied at 0.2% as opposed to 0.5% for
the commercial adjuvant.
Table 20
Sample All weeds XANST CHEAL ABUTH
Sample 13 5 1.24; A 92.56; A 62.5; A 41.39; A
Turbocharge 39.43; B 77.44; B 40; B 35; B
No adjuvant 23.61; C 45; C 24.44; C 25; C
EXAMPLE 20
In this example the rate response of the butylene oxide adjuvant 13 of Table 1
was measured to display the excellent performance of this adjuvant compared to the
commercial adjuvant ~ween~*20us,e d at a rate of 0.5% by volume. The herbicide
mesotrione was applied at rates of 30,60 or 90 grams per hectare by a laboratory track
15 sprayer to the weed species brachiaria platyphyla (BRAPL), digitaria sanguinalis
(DIGSA), and polygonum convolvulus (POLCO). Sample 13 was applied at a rate of
0.2% of the volume of the spray water. In each case the experiments were replicated four
times and the percentage damage to the weeds was assessed visually at time periods of 14
and 21 days after application.
20 The same statistical methodology that was applied in Example 3 was used here.
Table 21 shows the mean efficacy of the butylene oxide adjuvant 13 at a rate of
0.2% v/v with the pesticide-mesotrione compared to the adjuvant -Tween 20 applied at the
higher rate of 0.5%. The mean values and a letter denoting which group each adjuvant
belonged to are shown. As can be seen the butylene oxide adjuvant was more effective
25 than Tween 20 even though it was applied at 0.2% as opposed to 0.5 % for the
commercial adjuvant.
20
Table 21
Sample A11 weeds POLCO DIGSA BRAPL
-Sample l3--- -28239; A-- - 36.-1-I-; A -473--A-- - -39.A 4;-A--
Tween 20 26.1 I; B 32.77; B 45.55; A 26.1 1; B
No adjuvant 13.61; C 27.78; C 17.5; B 9.17; C
EXAMPLE 21
In this example the response of the butylene oxide adjuvant 13 of Table lwas
5 measured at an application rate of 0.2% of the volume of the spray solution used. It was
compared to the commercial tank mix adjuvant ~ t ~ l u sIF~, ~wh4ic1h w as applied at the
recommended rate of 0.5% by volume. The herbicide nicosufuron was applied at rates of
30,45 or 60 grams per hectare by a laboratory track sprayer to the weed species
chenopodium album (CHEAL), digitaria sanguinalis (DIGSA), and abutilon theophrasti
10 (ABUTH). In each case the experiments were replicated four times and the percentage
damage to the weeds was assessed visually at time periods of 14 and 2 1 days after
application.
The same statistical methodology that was applied in Example 3 was used here.
Table 22 shows the mean efficacy of the butylene oxide adjuvant 13 at a rate of
I5 0.2% vlv with the pesticide nicosulfuron compared to the adjuvant Atplus 4 1 1 F applied
at the higher rate of 0.5%. The mean values and a letter denoting which group each
adjuvant belonged to are shown. The data shows that the butylene oxide adjuvant was as
good as Atplus 41 1 F which was used at a higher rate than the butylene oxide adjuvant
(0.5% compared to 0.2%).
20 Table 22
Sample Allweeds DIGSA CREAL ABUTH
Sample 13 67.31; A 78.61; A 88.33; A 35; A
Atplus 41 1F 63.61; A 75.55; B 88.06; A 27.22; B
No adjuvant 8.1 1; B 4.05; C 0.56; B 19.72; C
EXAMPLE 22
In this example the response of the butylene oxide adjuvant 13 of Table 1 was
measured at an application rate of 0.2% of the volume of the spray solution used. It was
25 compared to the adjuvant tris 2-ethylhexyl phosphate [TEI-IP], which was applied at the
higher rate of 0.5% by volume. The herbicide pinoxaden was applied at rates of 7.5,
1 1.25 or 15 grams per hectare by a laboratory track sprayer to the weed species loliurn
perenne~(LOLPE),..aIopecurius_mposuirides..(ALOMY~),.and.avena.fatua..(ANEEA).-Ineach
case the experiments were replicated four times and the percentage damage to the
5 weeds was assessed visually at time periods of 14 and 21 days after application.
The same statistical methodology that was applied in Example 3 was used here.
Table 23 shows the mean efficacy of butylene oxide adjuvant 13 at a rate of 0.2%
V/V with the pesticide pinoxaden compared to the adjuvant tris 2-ethylhexyl phosphate
applied at the higher rate of 0.5%. The mean values and a letter denoting which group
I o each adjuvant belonged to are shown. The data shows that the butylene oxide adjuvant
was as effective as TEHP across the range of weed species tested.
Table 23
Sample All weeds LOLPE AVEFA ALOMY
Sample 13 58.05; A 53.89; B 76.94; A 43.33; A
TEHP 59.91; A 58.06; A 78.33; A 43.33; A
No adjuvant 3.43; B 2.22; C 6.39; B 1.67; B
EXAMPLE 23
In this example the rate response of 22 butylene oxide adjuvants of Table 1 were
measured at an adjuvant rate of 0.2% by volume, displaying excellent performance of
this adjuvant compared to the commercial adjuvant Turbocharge, which was used at a
rate of 0.5% by volume. The herbicide mesotrione was applied at rates of 60 or 120
20 grams per hectare by a laboratory track sprayer to the weed species brachiaria platyphyla
(BRAPP), digitaria sanguinalis (DIGSA), abutilon theophrasti (ABUTH) and amaranthus
retroflexus (AMARE). - In- each-case.the experiments were replicated four times andlhe- -.
percentage damage to the weeds was assessed visually at time periods of 14 and 21 days
after application. All the butylene oxide adjuvants were applied at a rate of 0.2% volume
25 of the spray water whereas Turbocharge was used at 0.5%.
The same statistical methodology that was applied in Example 3 was used here.
Table 23 shows the mean efiicacy of 22 butylene oxide adjuvants used at a rate of
0.2% v/v with the pesticide mesotrione compared to the adjuvant Turbocharge applied at
the higher rate of 0.5%. The mean values and a letter denoting which group each
30 adjuvant belonged to are shown. As can be seen most of the butylene oxide adjuvants
were more effective than Turbocharge even although they were applied at 0.2% as
opposed to 0.5% for the comtnercial adjuvant. All of the butylene adjuvants were as
Table 23
Sample Group Mean kill across weeds O/O
27 AB
26 ABC
2 1 ABCD 83.65
13 ARCDE 83.44
20 ABCDE 83.44
23 ABCDE 83.44
19 ABCDEF 83.13
7 ABCDEF 83.02
2 ABCDEF 82.60
6 ABCDEF 82.60
1 BCDEFG 8 1.98
22 CDEFGH 8 1.88
18 CDEFGH 81.77 .
25 CDEFGH 8 1.67
10 DEFGHI 81.35
17 EFGHI
11 FGHI
8 GI-IIJ
24 HIJ
--I6 IJ
Turbocharge J
5 J
No adjuvant K 69.48
EXAMPLE 24
In this example the responses of the butylene oxide adjuvants 7, 14,24 and 25 of
-Table-I-were measured-at an-application-rate of-0.2% of-the-volume-of the-spray-solution
used. They were compared to the adjuvant ~ r i j ~ ~w9hic6h ~wa,s applied at the same
5 rate. The herbicide pinoxaden was applied to the weed species lolium perenne (LOLPE),
alopecurius myosuirides (ALOMY), setaria viridis (SETVI) and avena fatua (AVEFA)
at rates of 7.5 or 15 grams per hectare by a laboratory track sprayer. Each experiment
was replicated three times and the percentage damage to the weeds was assessed visually
13 days after appIication.
10 The same statistical methodology that was applied in Example 3 was used here.
Table 25 shows the mean efficacy of 4 butylene oxide adjuvants used at a rate of
0.2% v/v with the pesticide pinoxaden compared to the adjuvant Brij 96V applied at the
same rate. The mean values and a letter denoting which group each adjuvant belonged to
are shown. The data shows that two of the butylene oxide adjuvants were more effective
15 than Brij 96V and two were as good as Brij 96V across the range of weed species tested.
Table 25
Sample Group Mean kill O h all weeds
7 A 72.3
2 5 B 57.3
Brij 96V B 55.0
24 B 52.9
No adjuvant C 16.3
-EX-AMPLE 25
In this example the rate responses of four butylene oxide adjuvants offable 1,
applied at 0.2%, displayed excellent performance when compared to the commercial
adjuvant ~ u r b o c h a r ~uese~d~ a,t a rate of 0.5%; and to tris 2-ethylhexyl phosphate
(TEHP) also used at 0.5%. The herbicide fomesafen was applied to the weed species
xanthium strumarium (XANST), abutilon theophrasti (ABUTH), setaria viridis (SETVI)
25 and chenopodium album (CHEAL) at rates of 60 or120 grams per hectare by a laboratory
track sprayer. Each experiment was replicated six times and the percentage damage to
the weeds was assessed visually at time periods of 7 and 13 days after application.
The same statistical methodology that was applied in Example 3 was used here.
Table 26 shows the mean efficacy of 4 butylene oxide adjuvants used at a rate of
-0.2% xlY_.with~the~pesticide~fomesafen~comparedtoatdhju ev.a nts..t ris. 2:ethylhexyl
phosphate (TEHP) and Turbocharge. The latter two adjuvants were applied at the higher
5 rate of 0.5% vlv. The mean values and a letter denoting which group each adjuvant
belonged to are shown along with the standard error. As can be seen the performance of
all four of the butylene oxide adjuvants was at least as good as the standard Turbocharge
and most of the adjuvants were as good as or better than TEHP.
Table 26
Sample Group Mean kill across weeds ( O h )
24 A 78.2
7 B 73.6
25 B
TEHP B
Turbocharge C
14 C
None D 47.0
EXAMPLE 26
In this example the rate response of sample 28 of Table 1, a non-ethoxylated
adjuvant, applied at 0.2% by volume was measured to display the performance of the
15 adjuvant compared to the commercial adjuvant Turbocharge, used at a rate of 0.5%. The
herbicide fomesafen was applied to the weed species xanthium strumarium (XANST),
abutilon theophrasti (ABUTH), setaria viridis (SETVI) and chenopodium album
- (CHEAL) at rates of 60 or 120 grams per hectare by a laboratory track sprayer. Each
experiment was replicated three times and the percentage damage to the weeds was
20 assessed visually at time periods of 14 and 21 days after application.
The same statistical methodology that was applied in Example 3 was used here.
Table 27 shows the mean efficacy of a non-ethoxylated butylene oxide adjuvant
used at a rate of 0.2% v/v with the pesticide fomesafen compared to the adjuvant
'l'urbocharge. Turbocharge was applied at the higher rate of 0.5%. The mean values and
25 a letter denoting which group each adjuvant belonged to are shown. As can be seen the
performance of the butylene oxide adjuvant was as good as the standard Turbocharge.
Table 27
.. .... .-.Sample .... Gro.up Mean..kill.(O/o) --.-
Turbocharge A 67.6
Sample 28 A 64.7
No adjuvant B 37.7
EXAMPLE 27
In this example the responses of sample 28 of table 1, a non-ethoxylated butylene
oxide adjuvant was compared to tris 2-ethylhexyl phosphate (TEHP). The butylene
oxide adjuvant was applied at an application rate of 0.2% by volume of the spray solution
used whereas TEHP was applied at 0.5%. The herbicide pinoxaden was applied to the
weed species lolium perenne (LOLPE), alopecurius myosuirides (ALOMY), setaria
10 viridis (SETVI) and avena fatua (AVEFA) at rates of 7.5 or 15 grams per hectare by a
laboratory track sprayer. Each experiment was replicated three times and the percentage
damage to the weeds was assessed visually 14 and 21 days after application.
The same statistical methodology that was applied in Example 3 was used here.
Table 28 shows the mean efficacy of a non-ethoxylated butylene oxide adjuvant
15 compared to TEHP with the pesticide pinoxaden. The rate of the former was 0.2%
whereas the latter was applied at 0.5%. The mean values and a letter denoting which
group each adjuvant belonged to are shown. The data shows that the butylene oxide
adjuvant was as effective as TEHP across the range of weed species tested.
Table 28
Sample Group Mean kill (Oh)
TEHP A 92.6
Sample 28 A 91.0
No adjuvant B 17.4
EXAMPLE 28
In this example the rate response of a non-ethoxylated butylene oxide adjuvant
25 was measured at an adjuvant rate of 0.2% by volume in order to display the excellent
performance of this adjuvant compared to the commercial adjuvant' Tween 20, which
was used at a rate of 0.5% by volume. The herbicide rnesotrione was applied at rates of
-45o-r -9.0. grams-per-hectare-by-a laboratory-track-sprayer- to-the-weed-species-brachiariadecumbens
(BRADE), digitaria sanguinalis (DIGSA), polygonum convolvulus
5 (POLCO) and amaranthus retroflexus (AMARE). In each case the experiments were
replicated three times and the percentage damage to the weeds was assessed visually at
time periods of 7, 14 and 2 1 days after application. The butylene oxide adjuvant was
applied at a rate of 0.2% of the volume of the spray water whereas Tween 20 was used at
0.5%.
10 The same statistical methodology that was applied in Example 3 was used here.
Table 29 shows the mean efficacy of an unethoxylated butylene oxide adjuvant
compared to Tween 20 with the pesticide mesotrione. The rate of the former was 0.2%
whereas the latter was applied at 0.5%. The mean values and a letter denoting which
group each adjuvant belonged to are shown. As can be seen the butylene oxide adjuvant
15 was as effective as Tween 20 even though it was applied at 0.2% as opposed to 0.5% for
the commercial adjuvant,
Table 29
Sample Group Mean kill %
Sample 28 A 68.8
Tween 20 A 65.8
No adjuvant B 47.2
EXAMPLE 29
2 o In this example the response of sample 28 of Table 1 , a non-ethoxylated butylene
oxide adjuvant was measured at an application rate of 0.2% of the volume of the spray
solution used. It was compared to the commercial tank mix adjuvant ~ t ~ l u s l1 1'F ~, 4
which was applied at the recommended rate of 0.5% by volume. The herbicide
nicosufuron was applied at rates of 30 or 60 grams per hectare by a laboratory track
25 sprayer to the weed species chenopodium album (CHEAL), digitaria sanguinalis
(DIGSA), setaria viridis (SETVI) and abutilon theophrasti (ABUTM). In each case the
experiments were replicated three times and the percentage damage to the weeds was
assessed visually at time periods of 14 and 2 1 days after application.
The same statistical methodology that was applied in Example 3 was used here.
Table 30 shows the mean efficacy of a non-ethoxylated butylene oxide adjuvant
compared to Atplus 41 1F with the pesticide nicosulfuron. The rate of the former was
0.2% whereas-the-latter--was-applied-a0t .5%.- The-mean-values and a-letter-denoting- -
which group each adjuvant belonged to are shown along with the standard error. The
5 data shows that the butylene oxide adjuvant was as good as Atplus 4 1 1F which was used
at a higher rate than the butylene oxide adjuvants (0.2% compared to 0.5%).
Table 30
Sample Group Mean kill %
ATPLUS 4 1 1 F A 90.4
Sample 28 A 89.2
No adjuvant B 75.0
10 EXAMPLE 30
This example shows that samples 29 and 30 from Table 1 behave as adjuvants for
fungicides used against the fungus septoria tritici. Wheat was sprayed with water at a
rate of 200 litres per hectare, the water containing either isopyrazam or epoxyconazole, at
a concentration which enabled a pesticide application rate of 0.6,2, 6 or 20 grams per
15 hectare. Sample 29 was added at a rate of 0.2% vlv of the spray volume used and
sample 30 was added at a rate of 0.1 % vlv. As a comparison to these adjuvants the same
formulation was tested without the adjuvant, as a standard. Each experiment was
replicated 12 times and the results were averaged at each rate. Plants were examined for
curative effects. The percentage disease on each sample was assessed visually and
20 averaged across the replicates at each rate. This was converted to a percentage control by
comparison to the disease level on plants which were sprayed using a blank spray
application where the pesticide was not included.
Table 3 1 shows the percentage septoria control for the two adjuvants used with the four
25 levels of isopyrazarn as well as the blank formulation. Table 32 shows the percentage
septoria control for the two adjuvants used with the four levels of epoxyconazole as well
as the blank formulation. In each case it can be seen that the adjuvants have improved
the performance of the fungicide.
Table 3 1
Isopyrazam
glha Control Sample 30 Sample 31
Table 32
Epoxyconazole Sample Sample
?Yha Control 30 3 1
20 29 99 100
6 11 99 99
2 22 88 90
0.6 4 45 54
EXAMPLE 3 1
5 This is an insecticide example: it shows that sample 28 from Table 1 behaves as an
adjuvant for the insecticide thiamethoxam against Aphis craccivora. The lower sides of
French bean leaves were infested with an aphid population Aphis craccivora of mixed
ages contained in clip cages. The upper sides of the leaves were sprayed with the test
solutions, 1 day after aphid infestation. French bean was sprayed with water at a rate of
10 200 litres per hectare, the water containing 3, 6, 12.5 and 25 ppm thiamethoxam.
Sample 28 was added at a rate of 0.1 % v/v of the spray volume used. As a comparison to
this adjuvant the same formulation was tested without the adjuvant, as a standard. 5 days
after spray application, the aphids were checked visually for mortality. Each experiment
was replicated twice and the results were averaged at each rate. In the control
I 5 experiment the beans were sprayed with water and no mortality was observed.
~ c t a rWa G~2~5 i s a commercial product containing thiarnethoxam
Table 33
5 EXAMPLE 32
This is a Phytotoxicity example: it shows that sample 28 from Table 1 is not phytotoxic
to soybean, French bean and Chinese cabbage. The plants were sprayed with water at a
rate of approximately 500 litres per hectare, the water containing 0.1% v/v or 0.2% v/v
adjuvant. The plants were assessed for phytotoxicity 7 days after spray application.
Treatment
- - -. - - - - - - - - -.
Actara WG25
Actara WG25
+ 0.1% v/v
sample 28
10 Each experiment was replicated twice and the results averaged. In the control
3ppm
Ahiamethoxam Yoo-.
mortality
0
50
6ppm
- thiamethoxam-YO-.
mortality
70
90
experiment the plants were sprayed with water and no phytotoxicity was observed. The
results show that the adjuvant sample 28 is safer to the crops than the alcohol ethoxylate
adjuvant Genapol0100.
--
12.5 ppm
- thiamethoxam-
% mortality
9 9
97.5
25 PPm
-thiamethoxam-
% mortality
100
100
15
~ e n a p o0l1~0 0~ i s a commercial surfactant from Clariant, an oleyl ethoxylate with 10
moles ethylene oxide.
Table 34
--
O.l%v/vSample28
0.2%v/v Sample 28
0. l%v/v Genapol
0 100
0.2%v/v Genapol
0100 I I 1 I
Soybean
% phytotoxicity
0
1
3.5
15
French bean
% phytotoxicity
0
0
5
10
Chinese cabbage
% phytotoxicity
0
0
2
10
We Claim:
1. A bioperformance enhancing composition comprising:
a bioperformance enhancing adjuvant of Formula (I) and at least one agrochemical
where BO is butylene oxide; n is from 1 to 12; RI is C4-~0all