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(19)    (11) Patent Number; ICE 175
(45) Date of grant: 08/10/2008
Konya Inclustrim Property Insiltute.
(12) PATENT
 
(73)    Owner: VALENT U.SA CORPORATION,
1333 NORTH CALIFORNIA BOULEVARD SUITE 600 WALNUT CREEK, CA 94596,
U.S.A.
(72) Inventor:
KINCADE, Robert, T. and East David
(74)    Agent/address for correspondence: Hamilton Harrison & Mathews, P.O. Box 30333-00100,
Nairobi
 
(54) Title:
INSECTICIDAL COMPOSITION AND METHOD FOR THE USE THEREOF
(57) Abstract:
An insecticidal composition includes (I) at least one compound of formula (1) wherein RI is bromine, chlorine, methyl, or ethyl, R2 is bromine, chlorine, or ethyl, R3 is hydrogen, halogen, or trifluoromethyl, Xis -0-, -S-, or -NH-, and n is 2, 3, or 4, and (2) at least one compound of formula (II) wherein R and RI independently are an alkyl, alkenyl, or alkynyl group containing up to carbon atoms, R2 ishydrogen, an alkyl group containing 1 to 18 carbon atoms, a cycloalkyl group containing 3 to 8 carbon atoms, an alkenyl group containing 2 to 18 carbon atoms, or an alkylnyl group containing 3 to 18 carbons atoms, A3 is hydrogen or an alkyl group containing 1 to 6 carbon atoms, and Y is -0- or -5-. A method for killing insects such as the tobacco budworm and other Lepidopteran pests of cotton includes applying an insecticidally effective amount of such a composition to an area to be treated.
tie
 
INSECTICIDAL COMPOSITION AND
METHOD FOR THE USE THEREOF
FIELD OF THE INVENTION
The present invention is directed to an insecticidal composition and to a method for the use thereof. in particular, the present invention is directed to an insecticidal composition which takes advantage of the
5 synergistic action of two particular insecticides and to a method of using the composition to kill insects such as the tobacco budworm and other Lepidopteran pests of cotton.
BACKGROUND OF THE INVENTION
The tobacco budworm and other Lepidopteran insects are IC    serious pests of cotton fruit (squares and bolls). Moderate or heavy
infestations can dramatically reduce lint yields.
The tobacco budworm, Heliothis virescens and cotton bollworm, Helicoverpa zea, have developed resistance to major classes of insecticides used to control them, as discussed in Martin et al., "Effects
15 of Selected Synergists on Insecticide Toxicity in Tobacco Budworm (Lepidoptera: Noctuidae) in Laboratory and Field Studies," J. Econ. Entomol. 90(3)723-731 (1997), Kanga at al., "Tolerance to Cypermethrin and Endosulfan in Field Populations of the Bollworm (Lepidoptera: Noctuidae) from Texas," J. Econ. Entomol. 89(3)583-589
20 (1998), Kanga et al., "Monitoring for Resistance to Organophosphorus, Carbamate, and Cyclodiene Insecticides in Tobacco Budworm Adults
1
 
(Lepidopteria: Noctuidae),* J. Econ. Entomol. 88(5)11444149 (1995), and Elzen et al., °Resistance to Pyrethroids, Carbamate, and Organophosphate Insecticides in Field Populations of Tobacco Budworms (Lepidoptera: Noctuidae) in 1990," J. Econ. Entomol.
5 85(6):2064-2072 (1992).
New and better control alternatives are always needed to maintain crop production and provide alternative chemistry for rotation purposes, as discussed in Laws, Delta Agricultural Digest, Intertec Publishing (1998).
10    While the compositions in the art have provided some control of
Lepidopteran pests of cotton, there has been a need in the art for significantly greater control.
SUMMARY OF THE INVENTION
An object of the present invention is to provide significantly
15 greater control of tobacco budworm, cotton bollworm, and other Lepidopteran pests of cotton than has bean provided previously in the art
Accordingly, the present inventors conducted extensive experimentation and, as a result, they achieved the present invention,
20 which provides a novel and highly effective, multi-chemistry alternative that provides synergistic results for the control of Lepidopteran insects on cotton and other crops on which they might be present.
2
 
In particular, the present invention is directed to an insecticidal composition comprising (1) at least one compound of formula (I):
 

 
R2
wherein R, is bromine, chlorine, methyl, or ethyl, R2 is bromine,
chlorine, or ethyl, R3 is hydrogen, halogen, or trifluoromethyl, X is -0-, -
5 8-, or -NH-, and n is 2, 3, or 4, and (2) at least one compound of formula (II):
/C-12, Iti-S714
-\k3
wherein R and Fe independently are an alkyl, alkenyl, or alkynyl group
containing up to 6 carbon atoms, R2 is hydrogen, an alkyl group
containing 1 to 18 carbon atoms, a cycloalkyt group containing 3 to 8
la carbon atoms, an alkenyl group containing 2 to 18 carbon atoms, or an alkynyl group containing 3 to 18 carbon atoms, R3 is hydrogen or an alkyl group containing 1 to 6 carbon atoms, and Y is -0- or -S-.
Also, the present invention is directed to a method of killing Lepidopteran insects comprising applying to an area to be treated an
15        insecticidally effective amount of a composition comprising (1) at least'
one compound of formula (1):
3
 
R2
wherein R1 is bromine, chlorine, methyl, or ethyl, R2 is bromine, chlorine, or ethyl, R3 is hydrogen, halogen, or trifluoromethyl, X is -0-, - S-, or -NH-, and n is 2, 3, or 4, and (2) at least one compound of formula (II):
0    I?
lt—Y It„C•-•V    (II)
10-.51— '4\3
5 wherein R and R1 independently are an alkyl, alkenyl or alkynyl group containing up to 6 carbon atoms, R2 is hydrogen, an alkyl group containing 1 to 18 carbon atoms, a cycioalkyl group containing 3 to B carbon atoms, an alkenyl group containing 2 to 18 carbon atoms, or an alkynyl group containing 3 to 18 carbon atoms, IR' is hydrogen or an
10 alkyl group containing 1 to 6 carbon atoms, and Y is -0- or -5-.
DETAILED DESCRIPTION OF THE INVENTION
One component of the composition of the present invention is a compound of formula (I):
 
Rx
where RI is bromine, chlorine, methyl, or ethyl, R2 is bromine, chlorine, 15    or ethyl, R3 is hydrogen, halogen, or trifluoromethyl, X is -0-, -5-, or -
4
 
NH-, and n is 2, 3, or 4. This compound and methods for its preparation are described in detail in WO 96/11909, which is incorporated herein by reference.
A particularly preferred compound within formula (I) is one in
5 which R, is chlorine, R2 is chlorine, R3 is hydrogen, X is -0-, and n is 3, i.e., 24312,6-dichloro-4-(3,3-dichloroprop-2-enyloxy)phenoxy]propoxy]- 5-(trifluoromethyl)pyridine (which has been revised from 3,5-dichloro-4- (34540 uoromethyt-2-pyridyloxy)propyloxy)-1 -(3,3-di chioro-2-
propenyloxy)benzene).
10    A compound of formula (I) can be prepared by the following
method.
A compound of formula (a)
    etc:Ho    a
mx    •0
wherein R, is bromine, chlorine, methyl, or ethyl, R2 is bromine, chlorine, or ethyl, X is -0-, -9-, or -NH-, and n is 2, 3, or 4, is reacted 15 with a compound of formula (b)
 
The reaction is preferably effected in an inert solvent in the presence of a suitable base.
Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-
5 dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C1-C4) ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichioromethane, chloroform, 1,2-dichloroethane and chlorobenzene;
10 hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.
Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide;
t5 carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., Ci-C4) such as sodium methoxide,
20 sodium ethoxide and potassium tert-butOxide; and organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzy lammonium chloride) may be
6
 
added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of formula (a).
The reaction temperature is usually set within the range of -20°C to 150°C or the boiling point of a solvent used in the reaction,
5        preferably -5°C to 100°C or the boiling point of a solvent used in the
reaction.
The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimoiar ratio or a ratio closer thereto.
10 After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or
I5    recrystallation.
Another component of the composition of the present invention is a compound of formula (II):
/01 „C-R,
R,
wherein R and Ri independently are an alkyl, alkenyl, or alkynyl group 20 containing up to 6 carbon atoms, R2 is hydrogen, an alkyl group
7
 
containing 1 to 18 carbon atoms, a cycloalkyl group containing 3 to 8 carbon atoms, an alkenyl group containing 2 to 18 carbon atoms, or an alkynyl group containing 3 to 18 carbon atoms, R° is hydrogen or an alkyl group containing 1 to 6 carbon atoms, and Y is -0- or -S-. This
5 compound and methods for its preparation are described in detail in U.S. Patents 3,176,600, 3,845,172, and 3,914,417, which are incorporated herein by reference.
A preferred compound within formula (H) is one in which R and R1 independently are a methyl, ethyl, ally' or alkenyl group, R2 is 10 hydrogen or an alkyl group, R.' is hydrogen, and Y is -0-.
A particularly preferred compound within formula (II) is one in which R, R' and R2 are methyl groups, R° is hydrogen, and Y is -0-. This compound is known as acephate and is commercially available, e.g., from the Chevron Chemical Company under the trade name
15 Orthene®.
The composition of the present invention comprises a mixture of at least one compound of formula (I) and at least one compound of formula (11). A particularly preferred composition of the present invention comprises a mixture of 24342,6-dichloro-4-(3,3-dichloroprop-
20 2-enyloxy)phenoxy]propoxy1-5-(trifluoromethyl)pyriciine    (hereinafter
referred to as ''S-1812" for convenience) and acephate.
In the composition of the present invention, the ratio of the compound of formula (I): the compound of formula (II) can vary
8
 
preferably from 1:3.3 to 1:127.8, more preferably from 1:3.3 to 1:64, even more preferably from 1:3.3 to 1:15, on a parts by weight basis. For example, the ratio of S-1812:acephate can vary from 1 part S¬1812:5 parts acephate to 1 part S-1812:127.8 parts acephate. As an
5 example within this range, the ratio of S-1812:acephate can vary from 1 part S-1812:16 parts acephate to 1 part 5-1812:127.8 parts acephate. As another example within this range, the ratio of S¬1812:acephate can vary from 1 part S-1812:5 parts acephate to 1 part S-1812:10 parts acephate.
10    Other components which can be present in the invention
composition include emulsifiers and solvents. For example, an emulsifiable concentrate formulation of S-1812 can be prepared using anionic-nonionic emulsifier blends such as Atlox 3454 and Atlox 3455, manufactured by Uniqema (formerly ICI Surfactants), and an aromatic
15 hydrocarbon solvent such as Solvasso 150, manufactured by Exxon Chemical Company. When added to water, this formulation of S-1812 forms a solution containing 8-1812 which can then be added to an acephate-containing solution to form a solution of the composition of the present invention.
20    Once formulated, the invention composition is useful in a
method for controlling Lepidopteran insects by application of the
composition onto the insecticidal habitat. In general, the invention
9
 
composition can be applied onto the habitat in an amount effective to be insecticidal to the insects.
In the solution application of the present invention, the invention composition can be dissolved in from about 3 gallons to about 10
5 gallons of water for application per acre, such that preferably at least about 0.063 lb and 0.5 lb of active ingredient (compounds of formula (I) and formula (II), respectively), more preferably from about 0.063 lb and 0.5 lb to about 0.1 lb and 0.75 lb of active ingredient is applied per acre.
to    The composition of the present invention has been
demonstrated in the laboratory and in the field to be highly effective against Lepidopteran insects, bollworm, beet armyworm, soybean looper, and tarnished plant bug, providing synergistic results as compared with the performance of the individual active ingredients. As
15 a result, the present invention provides excellent control of Lepidopteran pests of cotton and other crops on which they might occur.
The following examples illustrate specific embodiments of the present invention, but should not be construed as limiting the scope of
20 the claims in any way. All parts, percents, ratios and the like are by weight unless otherwise indicated.
10
 
EXAMPLES
Example 1
An S-1812-containing formulation identified as 'S-1812 0.83E0" was prepared by mixing the following components (wlv%):
5    S-1812 (active ingredient)    10.3%
Atlox 3454F (emulsifier)    2.0%
Atlox 3455F (emulsifier)    8.0%
Solvesso 150 (solvent)    79.7%
Total    100.0%

10    As set forth above, 8-1812 0.83EC has 10.3% ai on a wlv%
basis, i.e., 0.83 lb ai/gallon [(0.1 g ai/mI)(3785 m1/1gallon)(1 lb/454 g)].
0.2g of S-1812 0.83EC was added to 800 nil distilled H2O and stirred to give a 25 ppmai (parts per million active ingredient) solution. This solution was serially diluted by 300 ml stock/300 ml distilled H2O
15 to yield solution concentrations of 12.5, 6.25 and 3.13 ppmai.
0.02g of acephate (Orthene, technical grade, 98% pure) was added to 50 ml of S-1812 6.25 ppmai stock and 50 ml of 5-1812 3.13 ppmal stock to give 400 ppmai acephate + 6.25 ppmai S-1812, and 400 ppmai acephate + 3.13 ppmai S-1812 mixtures.
20    The above procedure was repeated with 0.01g of acephate to
yield 200 ppmai acephate + 6.25 or 3.13 ppmai S-1812 mixtures.
11.
 
The procedure set forth in the preceding paragraph was repeated with 100 ml of S-1812 3.13 or 6.25 ppmai stock to yield 100 ppmai acephate + 6.25 or 3.13 ppmai 5-1812 mixtures.
Solutions of acephate alone of the various concentrations were 5    prepared in a similar manner using distilled I-120.
The testing substrate was composed of 2.0 ml of prepared artificial tobacco budworm diet mix (aio-Sere) dispensed into the bottom of a clear one ounce cup. The diet was dispensed in such a way that the surface when dry was level and smooth (no pits).
10 0.2 ml of the test mixture was pipetted onto the surface of the diet. The treated diet was placed under a fume hood to dry the test solution onto the diet surface (approximately one hour).
After drying, one second mater tobacco budworm larvae was placed into each cup, and the cup was seated with a tight fitting, but
15 not airtight, lid. The cups were held at 25°C and 50% RH and evaluated after seven days. Larvae were rated as dead or alive at this point. There were 20 replicates per treatment with one cup = one replication.
The results of this testing are shown in Table 1 below.
12.
 
TABLE 1: SYNERGISM BETWEEN ORTHENE AND S-1812
IN A LABORATORY EXPERIMENT WITH SECOND
I NSTAR TOBACCO BUDWORM LARVAE
S-1812&    Increase
Orthene    S-1812    In %
Ppm ai    Mortality of
S-1812    Orthene Additive    +    Mixture Mixture
8-1812 %    Orthene %    %    Orthene %    Over
Ppm ai Mortality Ppm al Mortality Mortality Ppm ai    Mortality Additive
(Mixture)
3,133.133.13 6.25 6.25 6.25    5 100
5 200  5 400
30 100
30 200
30 400    10 5 30 10 530    15 10 35 40 5 360    3.13+100 3.13+200 3.13+400 6.25+100
625+400    35 25 75 65 6
100    20 15 40 25 30 40

As can be seen from the results presented above in Table 1, the
5  compounds of formulas (I) and (II) act synergistically together to increase the mortality rate beyond the sum of the rates for the compounds individually and thereby provide unexpectedly superior control of a Lepidopteran pest.
Example 2
10    Spray treatments were applied by a tractor mounted (highboy)
spray boom to cotton field plots in Greenville, Mississippi that
measured 40-50 ft by 13.2 ft by 13.2 ft with 3-4 replications per
treatment: Treatments were applied at 10 gallons of spray volume per
acre. Tank-mixes were made by measuring both compounds
15 independently and then adding them to the appropriate amount of
 
water to produce the spray mixture. Treatments were applied in July/August at approximately one week intervals.
Plots were evaluated by sampling all damaged and undamaged bolls on 10 plants per plot. Cotton plots were evaluated for yield by
5 machine picking the center two rows of each plot. The results are shown in Table 2 below.
14
 
TABLE 2: FIELD EFFICACY OF S-1812 + ORTHENE AGAINST
TOBACCO BUDWORM AND COTTON BOLLWORM IN COTTON
Trt    Application    No. of
Applications    Product    ConcIFM    Lb OA
Application Rate    Meth    `51 Damaged
Bella    Boils/
Plant    Yield-Lbs Seed Cotton!A
1        0    WIC                 555.30    3.87    843.55
2    ABCDE    6    Curacron    8E0    .500    FOSP    2633    8.70    1578.28
    ABODE        Larvin    3.2FL    .300    FOSP           
3    ABODE    5    AeamiXL    .68EC    .050    FOSP    1663    7.30    1823.16
4    ABODE    5    Karate    1.0E0    .040    FOSP    23.27    0.00    1687.10
6    AC    2    AsanaXL    .813EC    .050    FOSP    3890    5.63    1142.88
6    ABODE    5    Wham    905P    1.0    FOSP    21A0    7.10    1537.45
7    ABCDE    5    8-1812    .83EC    .150    FOSP    14.37    7.93    1972.82
8    AC    2    S-1812    .83EC    .150    FOSP    23.53    7.07     1551.05
9    ABODE    5    8-1812    .83EC    .076    FOSP    14.10    8.83    2204.12
    ABODE        Orthene    90SP    .500    FOSP           
            CV                34.34    23.20    15.04
            LSD                16.78    2.69    388.02

Trt = treatment
Conc(FM = concentration and formulation
5 FOSP = foliar spray method
ABCDE (under Application) = five applications, coded A, B, C, D & E
 
UTC = untreated cotton
Curacron = profenofos
Larvin = thiodicarb
Asana XL = esfenvalerate
5 Karate = lambda cyhalothrin
Orthene = acephate
EC = emulsifiable concentrate FL = flowable concentrate
10 SP = soluble powder
BEC has 8 lb ai/gallon
3.2FL has 3.2 lb ai/gallon .66EC has 0.66 lb al/gallon
15    1 .0EC has 1.0 lb ai/gallon
90SP has 90% ai on a per weight basis
.83EC has 0,83 lb aVgallon
CV = Coefficient of Variation (a statistic for comparison of like 20    experiments)
LSD = Fishers Least Significant Difference (a statistical method of comparing two means for significant difference by providing the smallest valid difference)
16
 
As can be seen from the data presented above in Table 2, a mixture of compounds of formulas (I) and (II) provides unexpectedly superior results with respect to reducing the percentage of damaged bolls, providing a higher number of bolls per plant, and providing a
5 higher yield in pounds of seed cotton per acre as compared with the use of compounds of formulas (I) and (II) individually and as compared with the use of other insecticides.
Example 3
Additional testing was conducted against a variety of 10 Lepidopteran pests as shown-in Table 3 below.
17
 
TABLE 3
Test Sable..
POOP Fast
Test Sabjeet go.
gepoctlug Standard
Coasent
Days After Opt        • 00533    G0503
SPOEI =MX
    1    2    3    1
    P1103    14.17    ROTE    0250
s DA-A 6 OA -A 6 DA-A 2 DA-C

Tot    Fora Pa    App1 reate Appl Appl
Ho    Product cone Tp    Rate Volt Meth coda
1    DTC    31.0 a 54.0 a    11.0 a 35.0 a
251.512    35 87    .05 1mA2JA Foal. AB= 21.0 06 7.8 c    6.0 a 7.0 de
2 096E201 90 SP    .75 =AI/A FOSP ABODE
a    52812    35 RV    .063 1202/2. POSP ABODE 14.0 b 17.8 be 0.0 a 10.0 ode
9 ORME= 90 SP    .5 2.3a2/2, FOSP 63002
4    01512    35 MP    .063 1.861/6. FOSP AMCD0 16.0 0. 9.5 be 9.5 a 6.0 de
4 611287S. 90 SP    .75 LUAI/A FOSP A6CD5
5 01812    05 217    .075 LBAI/A FOSP 6609E 16.0 b 12-5 be 11.1 a. 6.0 dm
S 011252213 90 SP    .5 2FA1IA POOP AFC=
6 6161:    35 R7    .1 Imm/A P003. AMCD2 13.0 b 13.3 be 10.5 a 6.0 de
6 CRTM282 00 SP    .33 1502/A 7057 A3000
7 40=592 90 SP    .33 IMAI/A POSP A6CO2 10.0 ab 14.5 be 15.0 a 17.0 bed
0 MUDDLE PO SP    .5 ISAI/A FOSP ABC= 11.0 b 54.5 a 11.8 a. 12.0 8-1
s 00282.52 SD SP    .75 1342/A 700.7 ABCDa 20.0 ab 24.0 abc 9.5 a 21.0 be
10 81512    35 OP    .05 2.3001/A POOP AFC= 16.0 b 22.0 abc 7.0 a 7.0 de
12 61812    35 OP    .063 7,363/A FOSP 000E 14.0 b 20.3 be 11.0 a 22.0 b
12 61812    25 mv    .075 LBAI/A. FOSP =COI 22.0 al. 43.0 ab 10.0 a 13, b-e
13 51812    35 RP    .1 2502/A POSP ABC. 19.0 ab 14.0 be 10.0 a 17.0 bed
14 TRACER    4 IC    .06 13AS/A POSP ASC. 10.0 b 0.8 be 3.8 a 3.0 a
Lap (Po.05)    12.60    29.32    7.09    10.11
s6an4mni2x0lation    8.82    20.67    5.52    7.07
Cv    51.02    90.07 57.79    52.12
Replicate 7    0.066    0.621 1.024    1.070
Replicate 7.01,C.7    0.0767    0,4904 0.1412    0.2121
l♦imataent P    1.408    2.401 0.790    0.105
Treatment PcOo(01    0.1677    0.0174 0.6558    0.0001
Means followed by *ma letter 4o not significantly differ (Pw.05, Duncan's Bev .2)
IS
 
TABLE 3 (CONTINUED)
Test Sierleeta
Camp
Pest            SPOE;    TRIM    LYLGI
Test Sub'ect No..                3    4
Reporting Standard            NOTF    NOTF    11058
Comment                    ADULT
Days After Trt            DA-C    2 DA-C    3 DA-C
Trt    Form    Pm    APP1    Rate    Appl Appl       
No    Vrodnet Cone    Tp    Rate    Unit    Heth Code       
1    UTC            16.5 a    6.8 a    0.120 a
2    S1512    35    WP    _os LEAS/A POSP ARC. 3.3 ed    2.5 de    0.030 ab
2    027113115    90    SP    .75    LOAM POSP ADC.       
3    21612    35    VP    .063    111AI/A POSP ABC. 1.5 d    2.3 do    0.050 ab
3    oRrae.    90    SP    .5    1.13AI/ApOSP ABC=       
01812    35    RP    .063    LEAS/A POOP AMO. 4.3 cd    1.3 e    0.000b
4    ORT112213    50    SP    .75    LMAI/A. POSP ARCM       
5    01812    35    RP    .075    INAX/A POOP ASC. 6.9 ed    2.8 dm    0.010 ab
5    ORM.=    90    SP    .5    IOWA POOP ABC=
•       
6    81812    35    OP    .1    LHAVA rest 50050 3.0 cd    2.3 de    0.020 ab
6    CET..    90    SP    .33    ISIAIJA POSP ANCOR       
7    ORTSZNE    90    SP    .93    LBAI/A POOP ABC91814.8 ale    5.6 abe    0.110 a
8    amomm    90    SP    .5    1.21A2/A POOP ABCDE20.5 abc    3.5 b-e    0.050 ab
9    0005530    90    SP    .75    LEAS/A POSP ABODE 8.5 bed    3.8 b-s    0.060 ab
10    51822    35    1/7    .05    LBA2/A FOS? A3623 6.0 cd    8.0 a-4    0.080 ab
11    61812    35    MP    .059    555115. POOP AEC. 6.8 cd    6.3 ab    0.060 ab
12    11812    30    RP    .075    LNAL/A POSP ARCM 7.0 od    3.3 cde    0.120
13    91822    35    NP    .1    ZEAS/A POSP ADC= 9,5 04    1.3 e    0.070 ab
14    TRACER    4    SC    .09    LEAS/A POSP ABC= 2.8 ed    1.3 e    O.OgO ab
LOS (P0.05)            7.12    2.63    0.0691
Standard Deviation CV            4.99
73.92    1.64
53.69    0.0624
202.7
Replicate F            1-638    8.198    0.341
Replicate Pr. (F) Treatment F            0.1963
2.259    0.0002
4.228    0.7961
1.353
Treatment Prob(P)            0.0021    0.0003    0.2261
Means followed by same letter do not significantly differ 0,05, Dwncan's New 0005)
18-A
 
TABLE 3 (CONTINUED)
Test Sub3e0ts
Crop
Pest    ODCC1 GROPU =RCA ARA=
Test SubDost mo.    5    6    7
Reporting standard    NO=    19050    NO50    Rome
COM..
Days After Tot    I DA-C 3 DA-C 3 DA-C 3 DA-c
Trt    Form Fla
NO    Product Cons Tp    Appl Rate    Appl Appl
Rata Unit    Meth Code               
I    UTC        0.230 abs    0.020 b    0.030 a    0.000 b
2    51012    25 MP    .05 LRAI/A 0002 .3121=0    0.240 abs    0.000 b    0.010 a    0.000 b
2    0228E=    90 SP    .75 LBAI/A FOSP AEC=               
9    51812    36 2919    .063 IBAI/A FOSP AMCO2    0.240 abo    0.000 b    0.010 a    0.000 b
3    ORTERM2    90 SP    .5 IRAI/A FOS? ABDO.               
4    51812    25 VP    .063 LEAS/A Po. 1600D2    0.120 0    0.010 b    0.000    a    0.010 a
4    ORTEENE    90 SP    .75 LEAS/A FOSP ABCDE               
5    511112    35 R7    .075 LEAS/A POOP ABC=    0.290 abo    0.000 b    0-010 a    0.000 b
02211113    90 SP    .5 LEAS/A FOSP ABCD2               
6    02.812    25 WP    .1 LEAS/A POOP AMC=    0.170 bo    0.010 b    0.010 a    0.000 b
6    =TEE=    90 SP    .33 LEAS/A FOSP AEC=               
7    WITS=    so sr    .33 LEAS/A 0020 222012    0.220 abe    0.020 b    0.010 a    0.000 b
8    ORTEENE    90 SP    .5 TEAS/A POOP ABCD2    0.330 Mb    0.000 b    0.000 a    0.000 b
2    COMM=    90 SP    .75 LEAI/A FOSP AECO0    0.260 db. 0.000 b    0.000 a    0.000 b
10    61012    35 VP    .05 LEAS/A POOP ABCDT    0.330 ab    0.000 b    0.020 a    0.000 b
11    51812    95 RE    .062 LEAS/A FOS? ABC=    0.200 abc    0.050 a    0.010    a    0.000 b
12    51012    35 RP    .070 12AS/A POOP ABC=    0.350 43    0.000 Ps    0.020 A    0.000 b
13    51812    35 WP    .1 LEAS/A FOSP AMC=    0.290 abs    0.000 b    0.020 a    0.000 b
14    TRACER    • SC    .00    POOP A.000    0.290 a    0.010 b    0.010 a    0.000 b
LSD (9..03)        0.1702    0.0272    0.0341    0.0077
Standard Deviation        0.1191    0.0191    0.0238    0.0054
CO        44.34    222.29    208.69    758.11
Replicate P        6.614    0.210    1.072    0.974
Replicate Pr00091        0.0027    0.6591    6.3721    0.4149
Treatment P Treatment Frob(F)        1.479
0.1692    2.177
'0.0306    0.526
0.8943    0.974
0.4927
means f0110ved by    letter do not significantly differ (Pa.05, penman, New mRT)

19
 
TABLE 3 (CONTINUED)
Test SIG40at6
Crop Pest
Test Sublect Ho.
Reporting Standard
comment
Days After Trt    GOSEJ
LYLGI    SPORT
2
80017    POSQ    0075
NYMPS
3 RR-. 2 DA-D 2 DA-D

grt    PoEa Pm
Po    Prodoct cone Tp    .1.14. Rata    ARyl Appi
Rate Unit    Neth c.d.           
1    UPC            0.100 ibc    49.0 a    25.3 bo
2    51812    35 VT    .05    1891/A POOP AMCDE    0.010 d    7.0 cd    13.3 be
2    122212313    SO SP    .75    LEAS/A POSY ANODE           
3    01812    35    RP    .063    LEAS/A FOSP A2CDE    0.030 cd    14.5 ed    6.0
3    ORTEERB    90    SP    .5    LEAS/A 70$1, A3C1E           
4    01512    35    05    .003    LEAS/A 005P AECDE    0.000 d    10.0 od    15.3 be
4    ORTEEME    90    SP    .75    ISAS/A FOSP ADCDE           
5    51512    35    VP    .075    LEAS/A FOSP ABC.    0.000 d    9.0 cd    25:6 bo
5    0181202E3    90    SP    .5    MBAS/A POOP A201           
6    61812    35
0055511090
6    O    VP
SW    .1
.33    LEAS/A FOSP ABCD11
LEAS/A POST ADC=    0.020 od    12.0 cd    '13.5 be
7    0312EC1IE    90    SP    .33    LEAS/A POOP A.D.    0.050 bed 29.0 b    72.3 a
8    ORTIMIE    90    SP    .5    2352/A POOP A.D.    0.420 od    14.0 od    65.5 m
9    ORM=    90    SP    .75    =AM FOSP AEC=    0.000 d    20.0 be    45.5 ab
10    01612    35    MP    .05    LEA1/3. POOP ABC=    0.100 abc    9.0 cd    30.5 bc
11    51812    35    MP    .063    LEASIA POOP AEI=    0.040 cd    8.0 cd    14.0 be
12    51512    35    117    .075    19.2/APOSP ASC.    0.130 lb    17.0 bed    5.5 be
23    51512    35    MP    .1    LEAS/A pOSP ABC.    0.100 abc 14.0 cd    3.5 0
14    TRACER    .4    SC    .09    LEAS/A FOSP 3.507 0-5.540 a    2.0 .    3.5 0
LSD (Pe:05) Standard Deviation            0.0746    12.07    32.57
                0.0522
58.71    5.00
55.9    23.00
56.56
                       
Replicate F                0.518    0.290    1.753
Replicate Proban Treatment F                0.6725
3.762    0.7608
6.722    0.1721
4.348
Treatment Probon                0.0007    0.0001    0.0002
Mamma followed by same letter do oot.significantly differ (Pv.05, Duncan, Mee MR2)
19-A
 
TABLE 3 (CONTINUED)
Test Subjects
Crop Pest
Test Subject No.
Reporting Standard
oment
mays After Trt    GOS11.7    GOS.
Taxa;
KOPF    NM?    •PDHO
2 DA-D

TME    Form PM    Appl Rate Appl Appl
So    Product cc.. Tp    Rate Unit moth Code
2    COO    6.0 ob. 29.8 d 37.65 a
2 51012    35 RV    .05 LRAI/A POOP ARC= 3.3 bo 61.0 bo 12.65 od
2 am= 90 SP    .75 /MAI/A POSY AMC=
3 21012    35 WP    .063 =ALIA re. A3002 1.5 e 69.3 abc 22.82 cd
3 ORTEENZ 90 SP    .2 LRAT/A POSY ABC.
4 22812    15 VP    .063 LBAVA FOSS ABC= 2.8 be 94,3 at 11.45 od
4 ORM. 90 SP    .75 IMAI/A POSP A3CO2    .
5 SI=    35 SP    .075 10A2/A POOP ARCM 2.3 be 71.3 abe 14.73 0d
5 0,928325 90 SP    .5 I2!51/A POOP ARCM
6 51812    95 WP    .1 IMAXIA POOP A5003 3.5 be 53.8 Ab 14.49 ed
6 CSTMEE 90 SP    .33 121A3/5 POSP A30102
7- COTE= 90 SP    .33 MMAT/A POOP 3.9652 8.5 a 52.0 c 20.00 ib
B OST=13 90 SP    .5 N2A1/A POSP ARC= 6.0:ab 54.3 0 33.40 ab
9 091OSCHE 90 SP    .75 2352/A FOSP ARCM 5.3 abe 57.5 0 22.03 be
10 51812    35 RD    .05 WAVA POOP ARCM 6.9.ab 75.2 ate 10.58 cd
11 01812    35 PP    .063 LMAI/A POOP ARC= 4.5 abo 60.5 be 9,02 ed
12 $1912    35 AT    .075 LBAI/A POOP ARCM 3.0 be 56.5 c 13.03 ed
13 52812    35 WP    .1 LEAM/A FOSP ARCOT 2.5 be 67.8 abo 7.30 d
14 TRACI,R    4 SC    .09 1021/A POOP ARCM 2.8 be 87.5 a    2.55 d
2.311 (P..05)
standard Dev-4,,ti. cv
Replicate 1,
Replicate Prob(F) Treatment
Treatment Prob(9)    3.65 2.56 60.65
5.853 0.0021 2.307 0.0221    21.58
15.10
23.22
6.190 0.0015 4.171 0.0003    11.261 7.880 48.07
0.061 0.4208 6.652 0.0001

means followed by some Setter' do not significantly differ (Po.05, Emmomm's New 8132)
20
 
Trt = treatment
tiTC = untreated cotton
5 WP = wettable powder
SP = soluble powder
SC = soluble concentrate
35 WP has 35% al on a per weight basis tO 90 SP has 90% ai on a per weight basis 4 SC has 4 lb aiigallon
FOSP = foliar spray method 15 GOSHJ = cotton
SPOEI = beet armyworm, Spodoptera exigua TRINI = cabbage looper, Trichoplusia ni LYGL1= Tarnished plant bug, Lygus lineolaris
20 COCCI = ladybird beetles
GEOPU = bigeyed bug
CHRCA = lacewings
ARACH = spider
25 PDSQ = percent damaged cotton squares
NOTE = number per 10 row feet using beat cloth sampling method NOSW = number per swing of a sweep net
NOSP = number of cotton bolls (fruits) per cotton plant
PDBO = percent damaged cotton bolls
30
6 DA-A = 6 days after application A
Tracer = Spinosyn A+ Spinosyn D
35 CV = Coefficient of Variation
LSD = Fisher's Least Significant Difference
A treatment is a particular insecticide or insecticide mixture being tested.
40
The number of replicates or replications is the number of times a treatment is identically repeated within the same test (for example, tested on 3-4 plots in a field test)..
21
 
As can be seen from the results presented above in Table 3, the mixture of compounds as in the present invention again provided unexpectedly superior results as compared with the compounds individually and as compared with another insecticidal Mixture.
5 While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof.
22-
 
AMENDED CLAIMS
[received by the International Bureau on 25 September 2000 (25.09.00);
original claims 1-10 amended; other claims unchanged (2 pages)]
What is claimed is:
1.    An insecticidal composition comprising synergistically
insecticidally effective amounts of (1) at least one compound of formula (I):
 

 
5 wherein R, is bromine, chlorine, methyl, or ethyl, R2 is bromine, chlorine, or ethyl, R3 is .hydrogen, halogen or trifitioromethyl, X is -0-, -S-, or -NH-, and n is 2, 3, or 4, and (2) at least one compound of formula (II):
R-V    C....R.
10 wherein R and R1 independently are an alkyl, alkenyl, or alkynyl group containing up to 6 carbon atoms, R2 is hydrogen, an alkyl group containing 1 to 18 carbon atoms, a cycloalkyl group containing 3 to carbon atoms, an alkenyl group containing 2 to 18 carbon atoms, or an alkynyl group containing 3 to 18 carbon atoms, A3 is hydrogen or an
15 alkyl group containing 1 to 6 carbon atoms, and Y is -0- or -S-.
29
 
7.    An insecticidal composition as in claim 6, wherein (A) the
24342 ,6-dichl o ro-4-(3,3-dichloroprop-2-enyl oxy)p hen oxAp ropoxy1-5- (trifluoromethyl)pyridine and (B) the acephate are present in an (A):(B) ratio of 1:5 to 1:127.8 on a parts by weight basis.
B.    An insecticidal composition as in claim 7, wherein (A) the
2-p-[2,6-dichloro-4-(3,3-dichloroprop-2-enyloxy)phenoxy]propoxyl-5- (trifluoromethyl)pyridine and (B) the acephate are present in an (A):(B) ratio of 1:16 to 1:127.8 on a parts by weight basis.
9.    An insecticidal composition as in claim 7, wherein (A) the
2-[312,6-dichloro-4-(3,3-dichloroprop-2-enyloxy)phenoxyjpropoxy]-5- (trifluorarnethyl)pyritine and (B) the acephate are present in an (A):(B) ratio of 1:5 to 1:10 on a parts by weight basis.
10.    A method for killing Lepidopteran insects, comprising applying to an area to be treated synergistically insecticidally effective amounts of a composition comprising (1) at least one compound of formula (I):
 
30

 

 

 

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