CA1081615A - Insecticide activators - Google Patents
Insecticide activatorsInfo
- Publication number
- CA1081615A CA1081615A CA259,917A CA259917A CA1081615A CA 1081615 A CA1081615 A CA 1081615A CA 259917 A CA259917 A CA 259917A CA 1081615 A CA1081615 A CA 1081615A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- compound
- insecticide
- activating factor
- propyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002917 insecticide Substances 0.000 title claims abstract description 52
- 239000012190 activator Substances 0.000 title abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 93
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 52
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 13
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- -1 methoxy, ethoxy Chemical group 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 102
- 230000003213 activating effect Effects 0.000 claims description 43
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 abstract description 7
- 231100000167 toxic agent Toxicity 0.000 description 16
- 239000003440 toxic substance Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 240000007113 Rumex obtusifolius Species 0.000 description 5
- 235000009422 Rumex obtusifolius Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000567412 Estigmene acrea Species 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 230000000361 pesticidal effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 235000000318 Bindesalat Nutrition 0.000 description 2
- 244000106835 Bindesalat Species 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 241000255985 Trichoplusia Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 241000208241 Tropaeolum Species 0.000 description 1
- 240000001260 Tropaeolum majus Species 0.000 description 1
- 235000004424 Tropaeolum majus Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Abstract of the Invention A composition of matter is described herein which is useful as an activator for insecti-cides. The activator composition is defined by the formula wherein R is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl and i-butyl; R1 is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, and i-butyl;
R2 is selected from the group consisting of phenyl, substituted phenyl wherein said substituents are selected from methyl, ethyl, i-propyl, t-butyl, methoxy, ethoxy and dimetylamino; phenalkyl and substituted phenalkyl wherein said substituents are selected from chlorine, methyl, i-propyl and methoxy.
R2 is selected from the group consisting of phenyl, substituted phenyl wherein said substituents are selected from methyl, ethyl, i-propyl, t-butyl, methoxy, ethoxy and dimetylamino; phenalkyl and substituted phenalkyl wherein said substituents are selected from chlorine, methyl, i-propyl and methoxy.
Description
~08161S
Bac~round of the Invention Among the many insecticidal compounds, the phthalimidio-thiophosphates have reached a relatively high degree of commercial success. These compounds are ~oxic to a large number of insect pests at different concentrations varying with the resistance of the insects mentioned. Some of these compounds are described in U.S. Patent No. 2,767,194, specifically N-(mercaptomethyl) phthalimide-S-(0,0-dimethylphosphorodithioate).
The endeavor to extend the usefulness of the thiophos-phates by increasing their effectiveness and lowering the cost has led to extensive studies on another class of biologically active chemicals, customarily referred to as synergists. Among the many synergists employed, the alkyl oxides, specifically, piperonyl butoxide, have been widely used. These compounds are described in U.S. Patent No. 2,485,681 and 2,550,737.
Detailed D ____~tion of the Invention It has been discovered that the thiophosphate compounds having insecticidal activity can be increased by using an activator having the formula ISl ~ -R
,, .
~ ~ .
~"
10 81 ~1 ~
wherein R is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl and i-butyl; ~ is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl and i-butyl; R2 is selected from the group consisting of phenyl, substituted phenyl wherein said substituents are selected from methyl, ethyl, i-propyl, t-butyl, methoxy J ethoxy and dimethylamino; phenalkyl and substituted phenalkyl wherein said substituents are selected from chlorine, methyl, i-propyl and methoxy.
These compounds are manufactured by reactin~ an appropriate phenol or phenalkyl compound with certain haloalkyl - phosphoro derivatives. After the end products are achieved, they are isolated and purified and admixed with the insecticidal compound. The amount of activator admixed therewith can range between about 1 to 0.1 to about 1 to 10 parts insecticidal com-pound to activator compound. After the insecticidal compound and activator compound are mixed together, they are applied to the habitat of the insect in a conventional manner.
In order to illustrate the merits of the present invention, the following examples are provided:
Example 1 O.O-Di~ethYl-O-phenYl phosphorothioate To a solution of 9.4 grams (0.1 mole) phenol in lOO ml tetrahydrofuran was added 4.4 grams (0.11 mole) powered NaOH
stirred until clear. A solution of 16.0 grams (0.1 mole) OJO-dimethyl phosphorochloridothioate in 25 ml tetrahydrofuran was added slowly to the sodium phenylate solution and refluxed for 30 minutes. Benzene (100 ml) was added to the mixture.
The resulting mixture was washed with 10% NaOH and twice with H20, dried over anhydrous MgS04 and the volitiles removed under reduced pressure to yield 2002 grams N30 1.5327.
:' 108~61S
Example 2 0.0-Diethyl-0-phenyl phosphorothioate The procedure of Example 1 was repeated, except 18.9 grams (0.1 mole) of 0,O-diethyl phosphorochloridothioate was used. The yield was 24.6 grams N30 1.5077, Additional compounds were synthesized in a similar manner using appropriate starting materials. These compounds are listed in the following table.
TABLE I
S~O-R
Compound Number R Rl R2 1 -CH3 -CH3 ~
Bac~round of the Invention Among the many insecticidal compounds, the phthalimidio-thiophosphates have reached a relatively high degree of commercial success. These compounds are ~oxic to a large number of insect pests at different concentrations varying with the resistance of the insects mentioned. Some of these compounds are described in U.S. Patent No. 2,767,194, specifically N-(mercaptomethyl) phthalimide-S-(0,0-dimethylphosphorodithioate).
The endeavor to extend the usefulness of the thiophos-phates by increasing their effectiveness and lowering the cost has led to extensive studies on another class of biologically active chemicals, customarily referred to as synergists. Among the many synergists employed, the alkyl oxides, specifically, piperonyl butoxide, have been widely used. These compounds are described in U.S. Patent No. 2,485,681 and 2,550,737.
Detailed D ____~tion of the Invention It has been discovered that the thiophosphate compounds having insecticidal activity can be increased by using an activator having the formula ISl ~ -R
,, .
~ ~ .
~"
10 81 ~1 ~
wherein R is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl and i-butyl; ~ is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl and i-butyl; R2 is selected from the group consisting of phenyl, substituted phenyl wherein said substituents are selected from methyl, ethyl, i-propyl, t-butyl, methoxy J ethoxy and dimethylamino; phenalkyl and substituted phenalkyl wherein said substituents are selected from chlorine, methyl, i-propyl and methoxy.
These compounds are manufactured by reactin~ an appropriate phenol or phenalkyl compound with certain haloalkyl - phosphoro derivatives. After the end products are achieved, they are isolated and purified and admixed with the insecticidal compound. The amount of activator admixed therewith can range between about 1 to 0.1 to about 1 to 10 parts insecticidal com-pound to activator compound. After the insecticidal compound and activator compound are mixed together, they are applied to the habitat of the insect in a conventional manner.
In order to illustrate the merits of the present invention, the following examples are provided:
Example 1 O.O-Di~ethYl-O-phenYl phosphorothioate To a solution of 9.4 grams (0.1 mole) phenol in lOO ml tetrahydrofuran was added 4.4 grams (0.11 mole) powered NaOH
stirred until clear. A solution of 16.0 grams (0.1 mole) OJO-dimethyl phosphorochloridothioate in 25 ml tetrahydrofuran was added slowly to the sodium phenylate solution and refluxed for 30 minutes. Benzene (100 ml) was added to the mixture.
The resulting mixture was washed with 10% NaOH and twice with H20, dried over anhydrous MgS04 and the volitiles removed under reduced pressure to yield 2002 grams N30 1.5327.
:' 108~61S
Example 2 0.0-Diethyl-0-phenyl phosphorothioate The procedure of Example 1 was repeated, except 18.9 grams (0.1 mole) of 0,O-diethyl phosphorochloridothioate was used. The yield was 24.6 grams N30 1.5077, Additional compounds were synthesized in a similar manner using appropriate starting materials. These compounds are listed in the following table.
TABLE I
S~O-R
Compound Number R Rl R2 1 -CH3 -CH3 ~
2 -CH3 -CH3 ~
3 -CH3 -CH3 ~ 3
4 -CH3 CH3 ~
-CH3 -CH3 ~ OCH3 6 -CH3 -CH3 ~
7 -CH3 -CH3 ~ CH3 lV81615 Compound Number R ~ R2 fH3 9 -CH3 -CH3 ~ CN3H3 -c~3 -CH
11 -CH3 -CH3 ~ CH3 ~ / 3 13 -CH3 -CH3 ~ CH3 Compound Number R ~ R2 11 -CH3 -CH3 ~ CH3 C ~ ~ H3 13 -CH3 -CH3 ~ CH3 . ~ CH /
/ CH \
fH3 CH3 /CH3 ~H3 16 -C\cH -\H -CH2-CH2-10 81~ 5 Compound Number R ~ CH R2 17 -CH3 -CH3 -1H-~
19 -CH3 -CH3 -fH--CH3 -CH3 -CH2-f~-23 -C3H7 -C3H7 ~
Cl H3 Cl H3 ~3 24 -fH -CIH
CH2 CIH CH2 fH
Compound Number R Rl R2 28 -C2H5 -C2H5 -CH2-C~2--C2H5 C2 5 ~ CH3 31 -C2H5 -C2H5 - ~ ~ 2 . / CH3 32 -C2H5 C2H5 ~ CH3 ~_ /
33 -C2H5 C2H5 ~ CH3 1081~;15 Compound Number R Rl --2 36 -C2H5 -C2H5 CH2 ~ Cl Cl 37 -C2H5 -C2H5 CH2 ~Cl 38 -C2H5 -C2H5 -CH2 ~ CH3 39 -C2H5 -C2H5 -CH2~ CH
- 40 -C2H5 -C2H5 CH2 (~;~OCH
41 -CH3 C2H5 ~
42 -CH3 ~n~C3H7 ~3 44 -C2H5 -n-C3H
-lQ-0 ~ 1 61 5 Insecticidal Evaluation A. Hou~efly lMusca dome~tica (L.)] (HF) The following procedure was used to test both 9US-ceptible and S-chlorothion resistant houseflies. Stock solutions containing lOO~ug/ml of the toxicant and 500Jug/ml of the activator are prepared using appropriate solvents. Toxicant and activator are combined in a 1 part toxicant: 5 parts activator ratio by adding equal aliquots of the stock solutions to one ml of a 0.2%
peanut oil in acetone spreading solution in a glass Petri dish 60 mm in diameter, The toxicant/activator film residue forms in the Petri dish as the solvents evaporate. The Petri dishes are placed in a circular cardboard cage, closed on the bottom with cellophane and covered on top with cloth netting. Twenty-five female houseflies are introduced into the cage and the percent mortality is recorded after 48 hours. LD-50 values are expressed in terms of~ug of toxicant per 25 ~ flies. The aliquots are varied to achieve desired toxicant/activator concentrations ran8ing from lOO~ug toxicant/500 ug activator per Petri dish to that at which 50qO mortality is obtained, Controls are identical to the above with the exception that the activator is omitted.
~, Black Bean Aphid ~Aphis fabae (Scop.)l (BBA) Nasturtium (Tropaeolum sp.) plants, approximately 2-3 inches tall, are transplanted into sandy loam soil in 3-inch clay pots and infe~ted with 50-75 aphids of mixed ages. Twenty-four hours later they are sprayed, to the point of runoff, with aqueous suspensions of the toxicant formulated as a 50 wettable powder and activator. The suspensions are prepared in equal alinuots of the toxicant and activator dissolved in tap water and diluted in a tap water solution. Test concentrations for both toxicant and activator ranged from 0.05% to that at which 5~/0 mortality is obtained. Mortality ~s recorded after 48 hours and the LD-50 values are expressed as percent ac~ive ingredient in the solutions.
C. Salt-marsh Caterpillar [EstiRmene acrea (Drury)]
(SMC) Test solutions are prepared by dissolving equal aliquots of the toxicant and activator in a 50-50 acetone-water solution. Sectlons of bitter dock (Rumex obtusifolius) leaves, 1-1.5 inches in length are immersed in the test solutions for 1-2 seconds and placed on a wire screen to dry. The dried leaf is placed on a moistened piece of filter paper in a Petri dish and infested with five third-instar larvae. Mortality of the larvae is recorded after 48 hours and the LD-50 values are expressed as per cent toxicant in the acetone-water solutions.
D. Cabbage Looper [Trichoplusia _] (CL) Same as Salt-marsh Caterpillar (C), except that leaves of white cabbage (Brassica oleracla) are utilized as the host plant rather than bitter dock.
E. Tobacco Budwonm ~Heliothis virescens (F.)~ (TBW) S~e as the Salt-marsh Caterpillar (C), except that leaves of Romaine lettuce (Latuca sativa) are utilized as the host plant rather than bitter dock.
F. Beet Armyworm [Spodoptera exiqua (Hubner)~ (BAW) Same as the Salt-marsh Caterplllar (C), except that leaves of Romaine lettuce (Latuca sativa) are utilized as the host plant rather than bitter dock.
1081f~15 Activatin~ Factor The Activating Factor is arrlved at by using the following formula from the expected response for a given com-bination of two insecticides:
A.F. - LD50 of Toxicant (~ 2 Experimental LD50 of Combination X ~ The ratio of the % or weight of the synergist to the % or weight of the toxicant.
Y - The ratio of ~he LD50 of the toxicant to the LD50 of the synergist.
The experimental LD50 of the combination is in tenms of ~he toxicant only.
The activating factor is, therefore, the ratio of the expected LD50 of the combination divided by the experimental It is noted that when the observed response is greater than the expected, the Activating Factor is greater than one.
This response is ~ynergism.
TABLE II
~~ HF BBA SMC CL TBW~ -BAW ~~
Insecticiidde* 5,000 .04 2.0 .1 .5 .2 Insect c e + Compound ~tl 30 .005 .03 .005 .005 .005 Compound ~1 > 10,000 >.25 >.1 >,1 >.1 >.1 Activating Factor 166.7 8.0 3.33 >10.0 > 16.16> 13.33 Insecticide*
+ Compound #2 25 .C07 .03 .01 .008 .01 Compound #2 10,000 >.05 .05 >.1 >.1 > .1 Activating Factor 57.14 5.7 1.66 > 5.0 ~ 10.4~ 6.66 Insecticide*
+ Compound #3 25.0 .03 >.05.01 .03 .02 Compound ~3 > 10,000 >.05 .05>.1 >.1 >.1 Activating Factor 200 1.33 1.0> 5.0 > 2.78> 3.33 Insecticide*
+ Compound #4 20.0 .007 >.05.02 .01 .007 Compound #4 8,000 >.05 >.1.05 >.1 >.1 Activating Factor 80.0 5.7 1.01.66 ~ 8.33 > 9.5 Insecticide*
+ Compound ~5 20 .04 .03.02 .005 Compound ~5> 10,000 >.05 .03>.1 >.1 Activating Factor 250 1.0 1.0> 2.5 > 13.33 *Insecticide ~ N-(mercaptomethyl) phthalimide-S-(0,0-dimethyl-phosphorodithioate).
108~615 ~F BBA SMCCL TBW BAW
Insecticide* 20 .007 >.1.007 .006 Compound #6 > 10,000 >,05 .1 .05 >.1 Activating Factor 250 5.7 1.0 4.76 ~ 11.11 .
Insecticide*
+ Compound ~7 20 .007 .03 .1 .006 Compound ~t7 ~ 10,000 ~.05 .05~.1 ~.1 Activating Factor 250 ~.05 .05>.1 > 11.11 -Insecticide*
+ Compound ~8 30 .002 .05.05 .006 Compound ~8 10,000 >.05 >.05.1 >.1 Activating Facto~ 47.6 20 1.0 1.0 11.11 Insecticide*
+ Compound #9 40 .002 .05.03 .007 Compound #9 > 10,000 >.05 .05 >.1 .07 Activating Factor 125 20.0 1.0> 1.66 9.5 Insecticide*
+ Compound ~10 80 .007 >.1>.05 .009 Compound t~10 10,000 >.05 >.1 >.1 ~.1 Activating Factor 47.6 7.14 1.101.0 7.41 .
Insecticide*
+ Compound ~11 40 .008 >.1 .03 .008 Compound ~11. 6,000 .05 >.1 .03 >.1 Activating Factor 24.2 5.0 1.0 1.0 > 8.33 . _ ~ .
*Insecticide = N-(mercaptomethyl) phthalimide-S-(0,0-dimethyl-phosphorodithioate).
HF BBA SMC CL TB~ BAW
Insectlcide*
+ Compound 11~12 > 100 .003 .1 .03 .008 Compound ~12 > 10,000 >.05 >.1 >.1 >.1 Activating Factor rul.0 13.33 1.0 > 1.66 ~ 8.33 Insecticide*
+ Compound ~13 > 100 .01 >.05 .003 .02 Compound ~13 > 10,000 >.05 >.05 >.1 >.1 Activating Factor ~v 1.0 4,0 1.0 >16.67 >3.33 Insecticide*
+ Compound ~14 30, ,008 -- .01 .02 Compound ~14 11,000 >.05 ~.05 >.1 >.1 Activating Factor 36,46 5.0 > 5.0 > 3.33 .
Insecticide*
+ Compound ~15 50 .003 >.05 .02 ,05 Compound ~15 710,000 >.05>.05 >.1 >.1 Activating Factor 100 13.33 1.0 > 2.5 > 1.33 Insecticide*
+ Compound ~n6 40 .005 >,1 .006 .007 Compound ~16 2,000 >.05 >.1 .03 .1 Activating Factor 9.26 8.0 1.0 3.84 > 9.5 . . _ . _ .
Insecticide*
+ Compound ~17 30 .008 .05 .02 .05 Compound #17 2,000 >.05 ~.1 .1 ~.1 Activating Factor 12.34 5.0 > 2.0 2.5 > 1.33 *Insecticide = N-(mercaptomethyl) phthalimide-S-(O,0-dimethylphos-phorodithioate).
108~615 ~ ~ HF BBA SMC CL TBW BAW
Insecticide*
+ Compound ~18 30 .007 .05 .03 .1 .007 Compound ~18 5,000> .05 .05 >,1 >.1 .1 Activating Factor 27.7 5,7 1.0> 1.66 > 1.0 9.5 -Insecticide*
+ Compound ~19 25 .02 >.05 .02 >.1 .06 Compound ~19 2,500>.05 >.05 ~.1 >.1 >.1 Factor 18.18 2.0 1.0> 2.5 ~vl.0 > 1.111 Insecticide*
+ Compound #20 40 .01 >.05 .02 .08 .008 Compound #2010,000 >.05 >.05 .09 >.1 >.1 Activating Factor 35.7 4.0 1.02.37 > 1.25 > 8.33 Insecticide*
+ Compound #21> 100. ,005 >,05,003 .07 .02 Compound #21> 10,000 >.05 >.05 >.1 >.1 >.1 Activating Factor 1.0 8.01.0 > 16.67> 1.42 > 3.33 Insecticide*
+ Compound #22 20 .003 .01.005 .005 .005 Compound #22 7,000>.25 .07 .1 >.1 .1 Activating Factor 54.7 13.33 7.010.0 > 16.67 13.33 Insecticide*
+ Compound ~23 35.0 .01 .01 .01 < .003 .008 Compound #23 10,000>.05 .01 .03 ~.03 .06 Activating Factor 40.8 4.0 1.0 1.0 -- 5.77 ~ .
*Insecticide = N-(mereaptomethyl) phthalimide-S-~0,0-dimethylphos-phorodithioate).
HF BBA SMC CL TBW BAW
+ Compound #2440 .03 .05 .01 .02 .008 Compound ~24>10,000 >.05 .05 .03 .09 >.1 Activating Factor125. 1.33 1.0 2.3 3.8 >8.33 Insecticide*
+ Compound #2580 .003 .03 .05 .02 .02 Compound ~25>10,000 >.05 .1 .05 .1 >.1 Activating Factor 62.5 13.33 3.33 1.0 4.1 >3.33 , Insecticide*
+ Com~ound #26 30.0 .02 .05 .02 .02 .007 Compound #26 ~10,000>.05 >.05 >.1 .1 >.1 Activating Factor 166.662.0 > 1.0 2.5 4.1 > 9.5 Insecticide*
Compound ~27 30 .02 .03 .02 .02 .007 Compound ~27 9,000>.05 .03 >.1 >.1 .08 Activating Factor 44.12 2.0 1.0 5,0> 4.1678,16 Insecticide*
+ Compound ~28 50 .01 .03 .005.009 .009 Compound t~8 9,000>.05 .03 .1 .1 >.1 Activating Factor 26.47 4.0 1.0 10.0 9.26 7.41 Insecticide*
+ Compound ~29 10 .003 >.1 .007.02 .01 Compound ~29 2,000>.05 >.1 >.1 >.1 >.1 Activating Factor 9.26 13.33 1.0 >7.14> 4.167> 6.66 .. . . . . .
*Insecticide = N-(mercaptomethyl) phthalimide-S-(0,0-dimethylphos-phorodithioate).
1~816~5 HF BBA SMC CL TBW BAW
Insecticide*
+Compound #3080 .01 .05.02 .005 ,Q2 Compound #30>10,000 >.05 >.05>.1 >.1 ~.1 Activating Factor 62.5 4.0 -- >2.5 >16.67 >3.33 Insecticide*
+ Compound #31 10 .01 >.05.02 >.003 .02 Compound #31 7,000>.05 >.05>.1 .1 >.1 Activating Factor 109.4 4.0 -- >2.5 > 27.8 >3.33 Insecticide*
+ Compound #32 30 .01 .05>.1 .07 .009 Compound ~32 >10,000>,05 >.05>.1 >.1 >.1 Activating Factor 166.664.0 -- -- >1.2 > 7.4 .
Insecticide*
+ Compound #33 35 .01 >.05.02 >.1 .02 Compound #33 > 10,000>.05 >,05>.1 >.1 >.1 Activating Factor 142.864.0 --~ 2.5 -- >3.33 Insecticide*
+ Compound #34 25 .01 >.05.03 ,003 .02 Compound #34 >710,000>.05 >,05>.1 >.1 >.1 Activating Factor 200 4.0 -->1.66 >27.8 >9.5 Insecticide*
+ Compound #35 30 .008 >.05.02 <.003 .01 Compound ~35 >10,000>.05 >.05.09 >.1 >.1 Activating Factor 166.675.0 -- 2.37 >27.8 > 6.66 *Insecticide s N-(mercaptomethyl) phthalimide-S-(O,O-dimethylphos-phorodiethioate).
1081~;~5 HF BBA SMC CL TBW BAW
Insecticide*
+ Compound ~36 60 .008 .05 .006 .007 .007 Compound #36 >10,000>.05 >.05 .06 <.03 .08 Activating Factor 83.335.0 -- 6.25 < 4.0 8.16 .
Insecticide*
+ Compound #37 40 .03 >.05 .02 .03 .009 Compound ~37 >10,000>.05 >.05 .09 .03 >.1 Activating Factor 1251.33 -- 2.37 1.0 7.41 Insecticide*
+ Compound ~38 30 >.05 .008 .005 .008 Compound #38 7,000~.05 >.05 >.1 .06 >.1 Activating Factor 36.46 -- >6.25 10.0 >8.33 .
Insecticide*
+ Compound #39 40 >.05 .02 <.003 .005 Compound #39 3,000>.05 >,05 >.1 .07 >.1 Activating Factor 13.4 -- 2.5 2.5 >13.33 -Insecticide*
+ Compound ~40 >100 >.05 .009 .07 .009 Compound ~40 7,000.05 ~.05 >.1 .1 ~.1 Activating Factor >10.94 -- >5.55 1.2 > 7.40 _ _ Insecticide*
+ Compound ~41 2.5 -- 0.03 0.007 .02 --Compound #41 >100 -- >0.1 0.07 > 0.1 --Activating Factor > 1.2 -- >3.2 5.9 > 4.1 --*Insecticide = N-(mercaptomethyl) phthalimide-S-(0,0-dimethylphosphoro-dithioate).
1 ~ 8 1 61 5 HF BBA SMC CL TI~W ~ AW---Insecticide*
+ Compound ~42 ~ 5 -- 0.02 0.007 0.02 --Compound ~42>lO0 -- 0.07 0.03 0.1 --Activating Fac~or >1.2 -- >3.4 3.3 4.1 --~ ~ ; -- . . . . .
Insecticide*
+ Compound ~t43 2.5 -- 0.02 0.003 0.07 --Compound #43>100 -- 0.07 0.03 > 0.1 --Activating Factor > 1.2 o- >3.4 7.7 ~1.2 --Insecticide*
+ Compound ~44 1.5 -- 0.02 0.007 0.02 --Compound ~K4>100 -- > 0.1 0.07 > 0.1 --Activating Factor > 2.0 -- > 4.7 2.2 > 4.1 --.
*Inqecticide - M-(mercaptomethyl) phthalimide-S-(0,0-dimethyl-phosphorodithioate) .
The compositions of this invention are generally embodied into a form suitable for convenient application. For example, the compositions can be embodied into pesticidal formulations which are provided in the form of emulsions, suspensions, solutions, dusts, and aerosol sprays. In general, such formulations will contain, in addition to the active compound, the adjuvants which are found normally in pesticide preparations. In these formulations, the active compounds of this invention can be employed as the sole pesticide component or they can be used in admixture with other compounds having similar utility. The pesticide for~ulations 10 8 ~ ~1 5 of this invention can contain, as ad~uvants, organic solvent~, such as sesame oil, xylene range solvents, heavy petroleum, etc.; water;
emulcifying agents; surface active agents; talc; pyrophyllite, diatomite; gypsum; clays; propellants, such as dichlorodifluoro-methane, etc. If desired, however, the active compositions can be applied directly to feedstuffs, seeds, etc., upon which the pests feed. Then applied in such a manner, it will be advantageous to use a composition which is not volatile. In connection with the activity of the presently disclosed pesticidal compositions, it should be fully understood that it i9 not necessary that they be active as such. The purposes of this invention will be fully served if the composition is rendered active by external influences, such as light, or by some physiological action which occurs when the compound is ingested into the body of the pest.
The precise manner in which the pesticidal compositions of this invention are used in any particular instance will be readily apparent to a person skillet in the art. Generally, the active pesticide composition will be embodied in the form of a liquid composition; for example, an emulsion, suspension, or aerosol spray. While the concentration of the active pesticide composition in the present formulation can vary within rather wide limits, ordinarily, the pesticide composition will comprise not more than about 50~0qO by weight of the formulation.
-CH3 -CH3 ~ OCH3 6 -CH3 -CH3 ~
7 -CH3 -CH3 ~ CH3 lV81615 Compound Number R ~ R2 fH3 9 -CH3 -CH3 ~ CN3H3 -c~3 -CH
11 -CH3 -CH3 ~ CH3 ~ / 3 13 -CH3 -CH3 ~ CH3 Compound Number R ~ R2 11 -CH3 -CH3 ~ CH3 C ~ ~ H3 13 -CH3 -CH3 ~ CH3 . ~ CH /
/ CH \
fH3 CH3 /CH3 ~H3 16 -C\cH -\H -CH2-CH2-10 81~ 5 Compound Number R ~ CH R2 17 -CH3 -CH3 -1H-~
19 -CH3 -CH3 -fH--CH3 -CH3 -CH2-f~-23 -C3H7 -C3H7 ~
Cl H3 Cl H3 ~3 24 -fH -CIH
CH2 CIH CH2 fH
Compound Number R Rl R2 28 -C2H5 -C2H5 -CH2-C~2--C2H5 C2 5 ~ CH3 31 -C2H5 -C2H5 - ~ ~ 2 . / CH3 32 -C2H5 C2H5 ~ CH3 ~_ /
33 -C2H5 C2H5 ~ CH3 1081~;15 Compound Number R Rl --2 36 -C2H5 -C2H5 CH2 ~ Cl Cl 37 -C2H5 -C2H5 CH2 ~Cl 38 -C2H5 -C2H5 -CH2 ~ CH3 39 -C2H5 -C2H5 -CH2~ CH
- 40 -C2H5 -C2H5 CH2 (~;~OCH
41 -CH3 C2H5 ~
42 -CH3 ~n~C3H7 ~3 44 -C2H5 -n-C3H
-lQ-0 ~ 1 61 5 Insecticidal Evaluation A. Hou~efly lMusca dome~tica (L.)] (HF) The following procedure was used to test both 9US-ceptible and S-chlorothion resistant houseflies. Stock solutions containing lOO~ug/ml of the toxicant and 500Jug/ml of the activator are prepared using appropriate solvents. Toxicant and activator are combined in a 1 part toxicant: 5 parts activator ratio by adding equal aliquots of the stock solutions to one ml of a 0.2%
peanut oil in acetone spreading solution in a glass Petri dish 60 mm in diameter, The toxicant/activator film residue forms in the Petri dish as the solvents evaporate. The Petri dishes are placed in a circular cardboard cage, closed on the bottom with cellophane and covered on top with cloth netting. Twenty-five female houseflies are introduced into the cage and the percent mortality is recorded after 48 hours. LD-50 values are expressed in terms of~ug of toxicant per 25 ~ flies. The aliquots are varied to achieve desired toxicant/activator concentrations ran8ing from lOO~ug toxicant/500 ug activator per Petri dish to that at which 50qO mortality is obtained, Controls are identical to the above with the exception that the activator is omitted.
~, Black Bean Aphid ~Aphis fabae (Scop.)l (BBA) Nasturtium (Tropaeolum sp.) plants, approximately 2-3 inches tall, are transplanted into sandy loam soil in 3-inch clay pots and infe~ted with 50-75 aphids of mixed ages. Twenty-four hours later they are sprayed, to the point of runoff, with aqueous suspensions of the toxicant formulated as a 50 wettable powder and activator. The suspensions are prepared in equal alinuots of the toxicant and activator dissolved in tap water and diluted in a tap water solution. Test concentrations for both toxicant and activator ranged from 0.05% to that at which 5~/0 mortality is obtained. Mortality ~s recorded after 48 hours and the LD-50 values are expressed as percent ac~ive ingredient in the solutions.
C. Salt-marsh Caterpillar [EstiRmene acrea (Drury)]
(SMC) Test solutions are prepared by dissolving equal aliquots of the toxicant and activator in a 50-50 acetone-water solution. Sectlons of bitter dock (Rumex obtusifolius) leaves, 1-1.5 inches in length are immersed in the test solutions for 1-2 seconds and placed on a wire screen to dry. The dried leaf is placed on a moistened piece of filter paper in a Petri dish and infested with five third-instar larvae. Mortality of the larvae is recorded after 48 hours and the LD-50 values are expressed as per cent toxicant in the acetone-water solutions.
D. Cabbage Looper [Trichoplusia _] (CL) Same as Salt-marsh Caterpillar (C), except that leaves of white cabbage (Brassica oleracla) are utilized as the host plant rather than bitter dock.
E. Tobacco Budwonm ~Heliothis virescens (F.)~ (TBW) S~e as the Salt-marsh Caterpillar (C), except that leaves of Romaine lettuce (Latuca sativa) are utilized as the host plant rather than bitter dock.
F. Beet Armyworm [Spodoptera exiqua (Hubner)~ (BAW) Same as the Salt-marsh Caterplllar (C), except that leaves of Romaine lettuce (Latuca sativa) are utilized as the host plant rather than bitter dock.
1081f~15 Activatin~ Factor The Activating Factor is arrlved at by using the following formula from the expected response for a given com-bination of two insecticides:
A.F. - LD50 of Toxicant (~ 2 Experimental LD50 of Combination X ~ The ratio of the % or weight of the synergist to the % or weight of the toxicant.
Y - The ratio of ~he LD50 of the toxicant to the LD50 of the synergist.
The experimental LD50 of the combination is in tenms of ~he toxicant only.
The activating factor is, therefore, the ratio of the expected LD50 of the combination divided by the experimental It is noted that when the observed response is greater than the expected, the Activating Factor is greater than one.
This response is ~ynergism.
TABLE II
~~ HF BBA SMC CL TBW~ -BAW ~~
Insecticiidde* 5,000 .04 2.0 .1 .5 .2 Insect c e + Compound ~tl 30 .005 .03 .005 .005 .005 Compound ~1 > 10,000 >.25 >.1 >,1 >.1 >.1 Activating Factor 166.7 8.0 3.33 >10.0 > 16.16> 13.33 Insecticide*
+ Compound #2 25 .C07 .03 .01 .008 .01 Compound #2 10,000 >.05 .05 >.1 >.1 > .1 Activating Factor 57.14 5.7 1.66 > 5.0 ~ 10.4~ 6.66 Insecticide*
+ Compound #3 25.0 .03 >.05.01 .03 .02 Compound ~3 > 10,000 >.05 .05>.1 >.1 >.1 Activating Factor 200 1.33 1.0> 5.0 > 2.78> 3.33 Insecticide*
+ Compound #4 20.0 .007 >.05.02 .01 .007 Compound #4 8,000 >.05 >.1.05 >.1 >.1 Activating Factor 80.0 5.7 1.01.66 ~ 8.33 > 9.5 Insecticide*
+ Compound ~5 20 .04 .03.02 .005 Compound ~5> 10,000 >.05 .03>.1 >.1 Activating Factor 250 1.0 1.0> 2.5 > 13.33 *Insecticide ~ N-(mercaptomethyl) phthalimide-S-(0,0-dimethyl-phosphorodithioate).
108~615 ~F BBA SMCCL TBW BAW
Insecticide* 20 .007 >.1.007 .006 Compound #6 > 10,000 >,05 .1 .05 >.1 Activating Factor 250 5.7 1.0 4.76 ~ 11.11 .
Insecticide*
+ Compound ~7 20 .007 .03 .1 .006 Compound ~t7 ~ 10,000 ~.05 .05~.1 ~.1 Activating Factor 250 ~.05 .05>.1 > 11.11 -Insecticide*
+ Compound ~8 30 .002 .05.05 .006 Compound ~8 10,000 >.05 >.05.1 >.1 Activating Facto~ 47.6 20 1.0 1.0 11.11 Insecticide*
+ Compound #9 40 .002 .05.03 .007 Compound #9 > 10,000 >.05 .05 >.1 .07 Activating Factor 125 20.0 1.0> 1.66 9.5 Insecticide*
+ Compound ~10 80 .007 >.1>.05 .009 Compound t~10 10,000 >.05 >.1 >.1 ~.1 Activating Factor 47.6 7.14 1.101.0 7.41 .
Insecticide*
+ Compound ~11 40 .008 >.1 .03 .008 Compound ~11. 6,000 .05 >.1 .03 >.1 Activating Factor 24.2 5.0 1.0 1.0 > 8.33 . _ ~ .
*Insecticide = N-(mercaptomethyl) phthalimide-S-(0,0-dimethyl-phosphorodithioate).
HF BBA SMC CL TB~ BAW
Insectlcide*
+ Compound 11~12 > 100 .003 .1 .03 .008 Compound ~12 > 10,000 >.05 >.1 >.1 >.1 Activating Factor rul.0 13.33 1.0 > 1.66 ~ 8.33 Insecticide*
+ Compound ~13 > 100 .01 >.05 .003 .02 Compound ~13 > 10,000 >.05 >.05 >.1 >.1 Activating Factor ~v 1.0 4,0 1.0 >16.67 >3.33 Insecticide*
+ Compound ~14 30, ,008 -- .01 .02 Compound ~14 11,000 >.05 ~.05 >.1 >.1 Activating Factor 36,46 5.0 > 5.0 > 3.33 .
Insecticide*
+ Compound ~15 50 .003 >.05 .02 ,05 Compound ~15 710,000 >.05>.05 >.1 >.1 Activating Factor 100 13.33 1.0 > 2.5 > 1.33 Insecticide*
+ Compound ~n6 40 .005 >,1 .006 .007 Compound ~16 2,000 >.05 >.1 .03 .1 Activating Factor 9.26 8.0 1.0 3.84 > 9.5 . . _ . _ .
Insecticide*
+ Compound ~17 30 .008 .05 .02 .05 Compound #17 2,000 >.05 ~.1 .1 ~.1 Activating Factor 12.34 5.0 > 2.0 2.5 > 1.33 *Insecticide = N-(mercaptomethyl) phthalimide-S-(O,0-dimethylphos-phorodithioate).
108~615 ~ ~ HF BBA SMC CL TBW BAW
Insecticide*
+ Compound ~18 30 .007 .05 .03 .1 .007 Compound ~18 5,000> .05 .05 >,1 >.1 .1 Activating Factor 27.7 5,7 1.0> 1.66 > 1.0 9.5 -Insecticide*
+ Compound ~19 25 .02 >.05 .02 >.1 .06 Compound ~19 2,500>.05 >.05 ~.1 >.1 >.1 Factor 18.18 2.0 1.0> 2.5 ~vl.0 > 1.111 Insecticide*
+ Compound #20 40 .01 >.05 .02 .08 .008 Compound #2010,000 >.05 >.05 .09 >.1 >.1 Activating Factor 35.7 4.0 1.02.37 > 1.25 > 8.33 Insecticide*
+ Compound #21> 100. ,005 >,05,003 .07 .02 Compound #21> 10,000 >.05 >.05 >.1 >.1 >.1 Activating Factor 1.0 8.01.0 > 16.67> 1.42 > 3.33 Insecticide*
+ Compound #22 20 .003 .01.005 .005 .005 Compound #22 7,000>.25 .07 .1 >.1 .1 Activating Factor 54.7 13.33 7.010.0 > 16.67 13.33 Insecticide*
+ Compound ~23 35.0 .01 .01 .01 < .003 .008 Compound #23 10,000>.05 .01 .03 ~.03 .06 Activating Factor 40.8 4.0 1.0 1.0 -- 5.77 ~ .
*Insecticide = N-(mereaptomethyl) phthalimide-S-~0,0-dimethylphos-phorodithioate).
HF BBA SMC CL TBW BAW
+ Compound #2440 .03 .05 .01 .02 .008 Compound ~24>10,000 >.05 .05 .03 .09 >.1 Activating Factor125. 1.33 1.0 2.3 3.8 >8.33 Insecticide*
+ Compound #2580 .003 .03 .05 .02 .02 Compound ~25>10,000 >.05 .1 .05 .1 >.1 Activating Factor 62.5 13.33 3.33 1.0 4.1 >3.33 , Insecticide*
+ Com~ound #26 30.0 .02 .05 .02 .02 .007 Compound #26 ~10,000>.05 >.05 >.1 .1 >.1 Activating Factor 166.662.0 > 1.0 2.5 4.1 > 9.5 Insecticide*
Compound ~27 30 .02 .03 .02 .02 .007 Compound ~27 9,000>.05 .03 >.1 >.1 .08 Activating Factor 44.12 2.0 1.0 5,0> 4.1678,16 Insecticide*
+ Compound ~28 50 .01 .03 .005.009 .009 Compound t~8 9,000>.05 .03 .1 .1 >.1 Activating Factor 26.47 4.0 1.0 10.0 9.26 7.41 Insecticide*
+ Compound ~29 10 .003 >.1 .007.02 .01 Compound ~29 2,000>.05 >.1 >.1 >.1 >.1 Activating Factor 9.26 13.33 1.0 >7.14> 4.167> 6.66 .. . . . . .
*Insecticide = N-(mercaptomethyl) phthalimide-S-(0,0-dimethylphos-phorodithioate).
1~816~5 HF BBA SMC CL TBW BAW
Insecticide*
+Compound #3080 .01 .05.02 .005 ,Q2 Compound #30>10,000 >.05 >.05>.1 >.1 ~.1 Activating Factor 62.5 4.0 -- >2.5 >16.67 >3.33 Insecticide*
+ Compound #31 10 .01 >.05.02 >.003 .02 Compound #31 7,000>.05 >.05>.1 .1 >.1 Activating Factor 109.4 4.0 -- >2.5 > 27.8 >3.33 Insecticide*
+ Compound #32 30 .01 .05>.1 .07 .009 Compound ~32 >10,000>,05 >.05>.1 >.1 >.1 Activating Factor 166.664.0 -- -- >1.2 > 7.4 .
Insecticide*
+ Compound #33 35 .01 >.05.02 >.1 .02 Compound #33 > 10,000>.05 >,05>.1 >.1 >.1 Activating Factor 142.864.0 --~ 2.5 -- >3.33 Insecticide*
+ Compound #34 25 .01 >.05.03 ,003 .02 Compound #34 >710,000>.05 >,05>.1 >.1 >.1 Activating Factor 200 4.0 -->1.66 >27.8 >9.5 Insecticide*
+ Compound #35 30 .008 >.05.02 <.003 .01 Compound ~35 >10,000>.05 >.05.09 >.1 >.1 Activating Factor 166.675.0 -- 2.37 >27.8 > 6.66 *Insecticide s N-(mercaptomethyl) phthalimide-S-(O,O-dimethylphos-phorodiethioate).
1081~;~5 HF BBA SMC CL TBW BAW
Insecticide*
+ Compound ~36 60 .008 .05 .006 .007 .007 Compound #36 >10,000>.05 >.05 .06 <.03 .08 Activating Factor 83.335.0 -- 6.25 < 4.0 8.16 .
Insecticide*
+ Compound #37 40 .03 >.05 .02 .03 .009 Compound ~37 >10,000>.05 >.05 .09 .03 >.1 Activating Factor 1251.33 -- 2.37 1.0 7.41 Insecticide*
+ Compound ~38 30 >.05 .008 .005 .008 Compound #38 7,000~.05 >.05 >.1 .06 >.1 Activating Factor 36.46 -- >6.25 10.0 >8.33 .
Insecticide*
+ Compound #39 40 >.05 .02 <.003 .005 Compound #39 3,000>.05 >,05 >.1 .07 >.1 Activating Factor 13.4 -- 2.5 2.5 >13.33 -Insecticide*
+ Compound ~40 >100 >.05 .009 .07 .009 Compound ~40 7,000.05 ~.05 >.1 .1 ~.1 Activating Factor >10.94 -- >5.55 1.2 > 7.40 _ _ Insecticide*
+ Compound ~41 2.5 -- 0.03 0.007 .02 --Compound #41 >100 -- >0.1 0.07 > 0.1 --Activating Factor > 1.2 -- >3.2 5.9 > 4.1 --*Insecticide = N-(mercaptomethyl) phthalimide-S-(0,0-dimethylphosphoro-dithioate).
1 ~ 8 1 61 5 HF BBA SMC CL TI~W ~ AW---Insecticide*
+ Compound ~42 ~ 5 -- 0.02 0.007 0.02 --Compound ~42>lO0 -- 0.07 0.03 0.1 --Activating Fac~or >1.2 -- >3.4 3.3 4.1 --~ ~ ; -- . . . . .
Insecticide*
+ Compound ~t43 2.5 -- 0.02 0.003 0.07 --Compound #43>100 -- 0.07 0.03 > 0.1 --Activating Factor > 1.2 o- >3.4 7.7 ~1.2 --Insecticide*
+ Compound ~44 1.5 -- 0.02 0.007 0.02 --Compound ~K4>100 -- > 0.1 0.07 > 0.1 --Activating Factor > 2.0 -- > 4.7 2.2 > 4.1 --.
*Inqecticide - M-(mercaptomethyl) phthalimide-S-(0,0-dimethyl-phosphorodithioate) .
The compositions of this invention are generally embodied into a form suitable for convenient application. For example, the compositions can be embodied into pesticidal formulations which are provided in the form of emulsions, suspensions, solutions, dusts, and aerosol sprays. In general, such formulations will contain, in addition to the active compound, the adjuvants which are found normally in pesticide preparations. In these formulations, the active compounds of this invention can be employed as the sole pesticide component or they can be used in admixture with other compounds having similar utility. The pesticide for~ulations 10 8 ~ ~1 5 of this invention can contain, as ad~uvants, organic solvent~, such as sesame oil, xylene range solvents, heavy petroleum, etc.; water;
emulcifying agents; surface active agents; talc; pyrophyllite, diatomite; gypsum; clays; propellants, such as dichlorodifluoro-methane, etc. If desired, however, the active compositions can be applied directly to feedstuffs, seeds, etc., upon which the pests feed. Then applied in such a manner, it will be advantageous to use a composition which is not volatile. In connection with the activity of the presently disclosed pesticidal compositions, it should be fully understood that it i9 not necessary that they be active as such. The purposes of this invention will be fully served if the composition is rendered active by external influences, such as light, or by some physiological action which occurs when the compound is ingested into the body of the pest.
The precise manner in which the pesticidal compositions of this invention are used in any particular instance will be readily apparent to a person skillet in the art. Generally, the active pesticide composition will be embodied in the form of a liquid composition; for example, an emulsion, suspension, or aerosol spray. While the concentration of the active pesticide composition in the present formulation can vary within rather wide limits, ordinarily, the pesticide composition will comprise not more than about 50~0qO by weight of the formulation.
Claims (41)
1. A composition comprising N-(mercaptomethyl) phthalimide-S-(O,O-dimethylphosphorodithioate) and an acti-vating amount of a compound having the formula wherein R is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl and i-butyl; R1 is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl and i-butyl and R2 is selected from the group con-sisting of phenyl, substituted phenyl wherein said substi-tuents are selected from the group consisting of methyl, ethyl, i-propyl, t-butyl, methoxy, ethoxy and dimethylamino;
phenalkyl and substituted phenalkyl wherein said substituents are selected from the group consisting of chlorine, methyl, i-propyl and methoxy, said composition being useful as an insecticide.
phenalkyl and substituted phenalkyl wherein said substituents are selected from the group consisting of chlorine, methyl, i-propyl and methoxy, said composition being useful as an insecticide.
2. The composition of Claim 1 wherein R is -CH3, R1 is -CH3 and R2 is .
3. The composition of Claim 1, wherein R is -CH3, and R2 is .
4. The composition of Claim 1, wherein R is CH3, R1 is -CH3 and R2 is .
5. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
6. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
7. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
8. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
9. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
10. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
11. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
12. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
13. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
14. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 an R2 is
15. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is
16. The composition of Claim 1, wherein R is , R1 is and R2 is .
17; The composition of Claim 1, wherein R is , R1 is and R2 is .
18. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
19. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
20. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
21. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
22. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
23. The composition of Claim 1, wherein R is -C2H5, R1 is C2H5 and R2 is .
24. The composition of Claim 1, wherein R is -C3H7, R1 is -C3H7 and R2 is .
25. The composition of Claim 1, wherein R is , R1 is and R2 is .
26. The composition of Claim 1, wherein R is , R1 is and R2 is .
27. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
28. The composition of Claim 1, wherein R is -CH3, R1 is -CH3 and R2 is .
29. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
30. The composition of Claim 1, wherein R is -C3H7, R1 is -C3H7 and R2 is .
31. The composition of Claim 19 wherein R is -C2H5, R1 is -C2H5 and R2 is .
32. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
33. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
34. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
35. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
36. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
37. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
38. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
39. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
40. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 amd R2 is
41. The composition of Claim 1, wherein R is -C2H5, R1 is -C2H5 and R2 is .
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/609,865 US4004001A (en) | 1974-01-14 | 1975-09-02 | Phosphorus containing insecticide activators |
| US609,865 | 1990-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1081615A true CA1081615A (en) | 1980-07-15 |
Family
ID=24442667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA259,917A Expired CA1081615A (en) | 1975-09-02 | 1976-08-26 | Insecticide activators |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5239628A (en) |
| AR (1) | AR216447A1 (en) |
| BE (1) | BE845794A (en) |
| BR (1) | BR7605696A (en) |
| CA (1) | CA1081615A (en) |
| CH (1) | CH619350A5 (en) |
| CS (1) | CS189029B2 (en) |
| DD (1) | DD126876A5 (en) |
| DE (1) | DE2639408A1 (en) |
| DK (1) | DK379176A (en) |
| ES (1) | ES451163A1 (en) |
| FR (1) | FR2322869A1 (en) |
| GR (1) | GR63183B (en) |
| HU (1) | HU178722B (en) |
| IN (1) | IN142443B (en) |
| NL (1) | NL7609670A (en) |
| PH (1) | PH11361A (en) |
| PL (1) | PL100062B1 (en) |
| PT (1) | PT65540B (en) |
| RO (1) | RO70090A (en) |
| SU (1) | SU803846A3 (en) |
-
1976
- 1976-08-23 DK DK379176A patent/DK379176A/en not_active Application Discontinuation
- 1976-08-23 IN IN1539/CAL/76A patent/IN142443B/en unknown
- 1976-08-24 JP JP51101029A patent/JPS5239628A/en active Pending
- 1976-08-26 CS CS765547A patent/CS189029B2/en unknown
- 1976-08-26 CA CA259,917A patent/CA1081615A/en not_active Expired
- 1976-08-27 HU HU76SA2967A patent/HU178722B/en unknown
- 1976-08-27 AR AR264494A patent/AR216447A1/en active
- 1976-08-27 RO RO7687383A patent/RO70090A/en unknown
- 1976-08-30 CH CH1098676A patent/CH619350A5/en not_active IP Right Cessation
- 1976-08-30 BR BR7605696A patent/BR7605696A/en unknown
- 1976-08-31 PT PT65540A patent/PT65540B/en unknown
- 1976-08-31 DD DD194539A patent/DD126876A5/xx unknown
- 1976-08-31 PH PH18851A patent/PH11361A/en unknown
- 1976-08-31 NL NL7609670A patent/NL7609670A/en not_active Application Discontinuation
- 1976-09-01 GR GR51595A patent/GR63183B/en unknown
- 1976-09-01 FR FR7626354A patent/FR2322869A1/en active Granted
- 1976-09-01 DE DE19762639408 patent/DE2639408A1/en not_active Withdrawn
- 1976-09-02 PL PL1976192162A patent/PL100062B1/en unknown
- 1976-09-02 ES ES451163A patent/ES451163A1/en not_active Expired
- 1976-09-02 SU SU762393508A patent/SU803846A3/en active
- 1976-09-02 BE BE7000877A patent/BE845794A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH619350A5 (en) | 1980-09-30 |
| NL7609670A (en) | 1977-03-04 |
| RO70090A (en) | 1982-09-09 |
| BR7605696A (en) | 1977-08-23 |
| HU178722B (en) | 1982-06-28 |
| DE2639408A1 (en) | 1977-03-10 |
| BE845794A (en) | 1977-03-02 |
| PL100062B1 (en) | 1978-08-31 |
| PT65540B (en) | 1978-02-22 |
| IN142443B (en) | 1977-07-09 |
| AR216447A1 (en) | 1979-12-28 |
| DK379176A (en) | 1977-03-03 |
| PT65540A (en) | 1976-09-01 |
| FR2322869A1 (en) | 1977-04-01 |
| JPS5239628A (en) | 1977-03-28 |
| CS189029B2 (en) | 1979-03-30 |
| PH11361A (en) | 1977-11-02 |
| ES451163A1 (en) | 1977-09-01 |
| SU803846A3 (en) | 1981-02-07 |
| DD126876A5 (en) | 1977-08-17 |
| FR2322869B1 (en) | 1980-11-07 |
| GR63183B (en) | 1979-10-03 |
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