ZA200502910B - 1,2,4-thiadiazole compounds and use thereof - Google Patents
1,2,4-thiadiazole compounds and use thereof Download PDFInfo
- Publication number
- ZA200502910B ZA200502910B ZA200502910A ZA200502910A ZA200502910B ZA 200502910 B ZA200502910 B ZA 200502910B ZA 200502910 A ZA200502910 A ZA 200502910A ZA 200502910 A ZA200502910 A ZA 200502910A ZA 200502910 B ZA200502910 B ZA 200502910B
- Authority
- ZA
- South Africa
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- group
- butynyl
- single bond
- formula
- pentynyl
- Prior art date
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
1,2,4-THIADIAZOLE COMPOUNDS AND USE THEREOF
The present invention relates to a 1,2,4-thiadiazole compound and use thereof.
It is known that a certain 1,3,4-thiadiazole compound can be used as an active ingredient of an agent for controlling harmful arthropods (DE3030661, etc.).
However, harmful arthropod controlling activity of this 1,3,4-thiadiazole compound is not sufficient, and a compound having more excellent harmful arthropod controlling activity is sought.
The present inventor has studied intensively in order to find out a compound having excellent pesticidal activity, and have found excellent harmful arthropod controlling - 20 activity in a 1,2,4-thiadiazole compound. Thus, the present invention has been completed.
That 1s, the present invention provides a 1,2,4- thiadiazole compound represented by the formula (1):
N—S XX
Rlo— J Je (1)
N A wherein R! represents a C3-C7 alkynyl group optionally substituted with one or more halogen atom(s), R? represents a halogen atom, a Cl1-C4 alkyl group, a Cl-C4 haloalkyl group, a C1l-C4 alkoxy group, a Cl-C4 haloalkoxy group, a
Cl1-C4 alkylthio group, a cyano group or a nitro group, n represents an integer of 0 to 5, provided that, when n represents an integer of 2 or more, respective R’s may be the same or different,
A represents an oxygen atom, a sulfur atom, a single bond, a CR’R* group or a NR’ group, R® and R? represent each . independently a hydrogen atom or a Cl1-C4 alkyl group, and
R®> represents a hydrogen atom, a Cl-C7 alkyl group, a Cl-C3 haloalkyl group, a C2-C4 (alkoxyalkyl) group, a C2-
C4 (haloalkoxyalkyl) group, a C3-C6 alkenyl group, a C3-Cé6 haloalkenyl group, a C3-C7 alkynyl group, a C3-C7 haloalkynyl group or a cyanomethyl group (herein after referred to as the compound of the present invention); and an arthropod controlling composition containing the same as an active ingredient.
In the compound of the present invention, examples of the C3-C7 alkynyl group optionally substituted with one or more halogen atom(s) represented by R' include a 2-propynyl group, a 2-butynyl group, a 4-fluoro-2-butynyl group, a 1- methyl-2-butynyl group, a 2-pentynyl group, a 4,4-dimethyl- 2-pentynyl group, a 3-chloro-2-propynyl group, a 3-bromo-2- propynyl group, a 3-iodo-2-propynyl group, a l-methyl-2- propynyl group, a 3-butynyl group, and a 3-pentynyl group.
Examples of the halogen atom represented by R? include a fluorine atom, a chlorine atom, and a bromine atom, examples of the C1l-C4 alkyl group represented by R? include a methyl group, an ethyl group, and a 1,l-dimethylethyl group, examples of the Cl-C4 haloalkyl group represented by
R? include a trifluoromethyl group, a difluoromethyl group, and a pentafluoroethyl group, examples of the C1-C4 alkoxy group represented by R? include a methoxy group and an ethoxy group, examples of the Cl-C4 haloalkoxy group represented by R? include a trifluoromethoxy group and a pentafluoroethoxy group, examples of the Cl-C4 alkylthio group represented by R? include a methylthio group, and an ethylthio group.
Examples of the CRR* group represented by A include a
CH, group, a CH(CHj) group, and examples of the NR? group represented by A include a NH group, a NCH; group, a NCpHs group, a NCH,OCHz group, a NCH;O0CzHs group and a NCHCN group.
Examples of the compound of the present invention include a 1,2,4-thiadiazole compound represented by the formula (1) wherein R! is a 2-propynyl group; a 1,2,4-
thiadiazole compound represented by the formula (1) wherein
R! is a 2-butynyl group; a 1,2,4-thiadiazole compound represented by the formula (1) wherein R! is a 2-pentynyl group; a 1,2,4-thiadiazole compound represented by the formula (1) wherein A is a single bond; a 1,2,4-thiadiazole compound represented by the formula (1) wherein R! is a 2- propynyl group, and A is a single bond; a 1,2,4-thiadiazole compound represented by the formula (1) wherein R! is a 2- butynyl group, and A is a single bond; a 1,2,4-thiadiazole compound represented by the formula (1) wherein R! is a 2- pentynyl group, and A is a single bond; a 1,2,4-thiadiazole compound represented by the formula (1) wherein n is 0; a 1,2,4-thiadiazole compound represented by the formula (1) wherein n is 1 or 2, and R? is a halogen atom.
Then, a process for preparing the compound of the present invention will be explained. The compound of the present invention can be prepared, for example, by reacting a compound represented by the formula (2) and ROH in the presence of a base.
R'OH
HiC-s Pa 7 ’ od 3 )n (Ohm 1) (2) wherein A, RY, R? and n are as defined above, and m represents 1 or 2.
The reaction is usually performed in a solvent.
Examples of the solvent to be used include ethers such as tetrahydrofuran, acid amides such as N,N-dimethylformamide, dimethyl sulfoxide, and a mixture thereof. Examples of the 5 base used in the reaction include inorganic bases such as sodium hydride, and the amount of the base is usually 1 to 2 mole relative to 1 mole of a compound represented by the formula (2). The amount of R'OH used in the reaction is usually 1 to 1.2 moles relative to 1 mole of a compound represented by the formula (2). The reaction temperature is usually in a range of 0 to 80°C, and the reaction time is usually in a range of 1 to 24 hours.
After completion of the reaction, the compound of the present invention can be obtained by subjecting the reaction mixture to post-treatment procedures such as organic solvent extraction, and concentration. If necessary, the compound of the present invention can be further purified by subjecting to procedures such as chromatography.
The compound represented by the formula (2) can be prepared by reacting a compound represented by the formula (3) with an oxidizing agent.
N-S N-S ES 3 wa, H.C 3 ow
HGS NTA 328" NTA (Om (3) (2) wherein A, R?, n and m are as defined above.
The reaction is usually performed in a solvent.
Examples of the solvent to be used include halogenated hydrocarbons such as chloroform and dichloromethane, and a mixture thereof. Examples of the oxidizing agent used in the reaction include peracids such as 3-chloroperoxybenzoic acid, and the amount of the oxidizing agent is usually 1 to 2.5 moles relative to 1 mole of the compound represented by the formula (3). The reaction temperature is usually in a range of -5°C to room temperature, and the reaction time is usually in a range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (2) can be obtained by subjecting the reaction mixture to post-treatment procedures such as organic solvent extraction, and concentration. If necessary, the compound can be further purified by subjecting to procedures such as chromatography.
The compound represented by the formula (3) can be prepared by any of the following methods of (I) to (IV) depending on a kind of A in the formula (3). (I) A process for preparing a compound represented by the formula (3) in which A is a single bond, by reacting 5- chloro-3-methylthio-1,2,4-thiadiazole, and a phenylboronic acid compound represented by the formula (4) or a trialkylphenyltin compound represented by the formula (5) in the presence of a transition metal compound.
JEN!
N-S (HO),B "
Hes” Wel or je: a yet et (R?), (Rn H3CS™ 'N (R)sSn (5) wherein R? and n are as defined above, and R® represents a
Cl-C4 alkyl group.
The reaction is usually performed in a solvent under an atmosphere of an inert gas (nitrogen, argon etc.).
Examples of the solvent used in the reaction include alcohols such as methanol, ethanol and 2-propanol, ethers such as 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane, and methyl-t-butyl ether, aromatic hydrocarbons such as benzene and toluene, ketones such as acetone, acid amides such as N,N-dimethylformamide, water, and a mixture thereof.
Examples of the transition metal compound used in the reaction include palladium (II) acetate, tetrakis (triphenylphosphine)palladium (0), {1,1'- bis (diphenylphosphino) ferrocene}dichloropalladium (II) and dichloro bis (triphenylphosphine)palladium(II), and the amount of the transition metal compound is usually 0.001 to 0.1 mole relative to 1 mole of 5-chloro-3-methylthio-1,2,4- thiadiazole. The amount of the phenylboronic acid compound represented by the formula (4) or the trialkylphenyltin compound represented by the formula (5) used in the reaction is usually 0.9 to 1.5 mole relative to 1 mole of 5~chloro-3-methylthio-1,2,4-thiadiazole. The reaction temperature of the reaction is usually in a range of room temperature to 150°C. The reaction time is usually in a range of 1 to 12 hours.
The reaction can be performed by adding a base, if necessary. Examples of the base which can be used include potassium phosphate, sodium carbonate, sodium bicarbonate, sodium acetate, potassium acetate and barium hydroxide. In addition, the reaction can be performed by adding a phase transfer catalyst, if necessary. Examples of the phase transfer catalyst which can be used include a quaternary ammonium salt such as tetrabutylammonium bromide, and benzyltrimethylammonium bromide.
After completion of the reaction, the objective product can be obtained by subjecting the reaction mixture to post-treatment procedures such as organic solvent extraction, and concentration. When the trialkylphenyltin compound represented by the formula (5) is used in the reaction, the objecte product can be obtained by adding an aqueous potassium fluoride solution to the reaction mixture, filtering the resulting precipitate, and concentrating the filtrate. The product can be further purified by subjecting to procedures such as chromatography, if 3 necessary. (ITI) A process for preparing a compound represented by the formula (3) in which A is an oxygen atom, a sulfur atom or a NH group, by reacting 5-chloro-3-methylthio-1,2,4- thiadiazole and a compound represented by the formula (6) in the presence of a base.
SE oe — 17 (Sw
Hic” NC LES RE (6) wherein R? and n are as defined above and Al represents an oxygen atom, a sulfur atom or a NH group.
The reaction is usually performed in a solvent, and examples of the solvent used in the reaction include ethers such as tetrahydrofuran, acid amides such as N,N- dimethylformamide, dimethyl sulfoxide, and a mixture thereof. Examples of the base used in the reaction include inorganic bases such as sodium hydride, and the amount of the base is usually 1 to 2 mole relative to 1 mole of 5- chloro-3-methylthio-1,2,4-thiadiazole. The amount of the compound represented by the formula (6) used in the reaction is usually 1 to 1.2 mole relative to 1 mole of 5-
chloro-3-methylthio-1,2,4-thiadiazole. The reaction temperature is usually in a range of 0 to 80°C, and the : reaction time is usually in a range of 1 to 24 hours.
After completion of the reaction, the objective product can be obtained by subjecting the reaction mixture to post-treatment procedures such as organic solvent extraction, and concentration. If necessary, the product can be further purified by subjecting to procedures such as chromatography. (III) A process for preparing a compound represented by the formula (3) in which A is a NR’ group, by reacting a compound represented by the formula (3) in which A is a NH group with RX in the presence of a base.
N-S NY, RX N=S N
A Ja h——= I A. ro
H3CS” “N” ON H3CS” “NN
H ls
R wherein R?, R®> and n are as defined above, and X represents a halogen atom.
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, acid amides such as N,N- dimethylformamide, dimethyl sulfoxide, and a mixture thereof. Examples of the base used in the reaction include inorganic bases such as sodium hydride, and the amount of the base is usually 1 to 2 mole relative to 1 mole of a compound represented by the formula (3) in which A is a NR® group. The amount of R°X used in the reaction is usually 1 to 1.2 mole relative to 1 mole of a compound represented by the formula (3) in which A is a NR® group. The reaction temperature is usually in a range of 0 to 80°C, and the reaction time is usually in a range of 1 to 12 hours.
After completion of the reaction, the objective product can be obtained by subjecting the reaction mixture to post-treatment procedures such as organic solvent extraction, and concentration. If necessary, the product can be further purified by subjecting to procedures such as chromatography. (IV) A process for preparing a compound represented by the formula (3), wherein A is a CR’R? group, by reacting 5- chloro-3-methylthio-1,2,4-thiadiazole and a compound represented by the formula (7) in the presence of a transition metal compound.
N-S Pes - + BrZn n N—S
Hes” We AW z= A 3 3
R® R H3CS™ NN 3 WL4 (7) R” R wherein R?% R?, RY and n are as defined above.
The reaction is usually performed in a solvent, and examples of the solvent used in the reaction include ethers such as tetrahydrofuran, acid amides such as N, N-
dimethylformamide, dimethyl sulfoxide, and a mixture thereof.
Examples of the transition metal compound used in the reaction include tetrakis(triphenylphosphine)palladium (0), {1,1’ -bis(diphenylphosphino) ferrocene}dichloropalladium (IT) and dichloro bis (triphenylphosphine)palladium (II), and the amount of the transition metal compound is usually 0.001 to 0.1 mole relative to 1 mole of 5-chloro-3- methylthio-1,2,4-thiadiazole.
The amount of a compound represented by the formula (7) used in the reaction is usually 1 to 1.2 mole relative to 1 mole of 5-chloro-3-methylthio-1,2,4-thiadiazole.
The reaction temperature is usually in a range of 0 to 80°C, and the reaction time is usually in a range of 1 to 24 hours.
After completion of the reaction, the objective product can be obtained by subjecting the reaction mixture to post-treatment procedures such as organic solvent extraction, and concentration. 1f necessary, the product can be further purified by subjecting to procedures such as chromatography.
Then, specific examples of the compound of the present invention are shown in Table 1.
: Table 1
Compound represented by the formula (1):
N—S | N X
Ro— PY (Rs (1)
N A
Compound (RY) 4 A
Ea RE SG 1 2-propynyl Unsubstituted Single bond 2 2-butynyl Unsubstituted Single bond 3 2-pentynyl Unsubstituted Single bond 4 4,4-dimethyl~- |Unsubstituted Single bond 2-pentynyl 5 2-butynyl 2-fluoro Single bond 6 2-butynyl 3-fluoro Single bond 7 2-butynyl 4-fluoro Single bond 8 2-butynyl 2-chloro Single bond 9 2-butynyl 3-chloro Single bond 2-butynyl 4-chloro Single bond 11 2-butynyl 2,4-difluoro Single bond 12 2-butynyl 2,5-difluoro Single bond 13 2-butynyl 2,6-difluoro Single bond 14 2-butynyl 3,4-difluoro Single bond 2-butynyl 3,5-difluoro Single bond 16 2-butynyl 2,3-difluoro Single bond 17 2-butynyl 2-methyl Single bond 18 2-butynyl 3-methyl Single bond 19 2-butynyl 4-methyl Single bond 2-butynyl 4-tert-butyl Single bond 21 2-butynyl 3,5- Single bond bistrifluoromethyl
Table 1 (contd.)
Compound (Rn A
Fa A Li CR 22 2-butynyl Unsubstituted "| Oxygen atom 23 2-butynyl 2-fluoro Oxygen atom 24 2-butynyl 3-fluoro Oxygen atom 2-butynyl 4-fluoro Oxygen atom 26 2-butynyl 2-chloro Oxygen atom 27 2-butynyl 3-chloro Oxygen atom 28 2-butynyl 4-chloro Oxygen atom 29 2-butynyl 2,4-difluoro Oxygen atom 2-butynyl 2,5-difluoro Oxygen atom 31 2-butynyl 2,6-difluoro Oxygen atom 32 2-butynyl 3,4-difluoro Oxygen atom 33 2-butynyl 3,5-difluoro Oxygen atom 34 2-butynyl 2,3-difluoro Oxygen atom 2-butynyl 2-methyl Oxygen atom 36 2-butynyl 3-methyl Oxygen atom 37 2-butynyl 4-methyl Oxygen atom 38 2-butynyl 4-tert-butyl Oxygen atom 39 2-butynyl 3,5- Oxygen atom bistrifluoromethyl 40 2-butynyl Unsubstituted CH, 41 2-butynyl 2—-fluoro CH» 42 2-butynyl 3-fluoro CH: 43 2-butynyl 4-fluoro CH, 44 2-butynyl 2-chloro CH» 45 2-butynyl 3-chloro CH: 46 2-butynyl 4-chloro CH; 47 2-butynyl 2,4-difluoro CH:
Table 1 (contd.)
Compound R (R%) an A
Sa A CE 48 2-butynyl 2,5-difluoro CH» 49 2-butynyl 2,6-difluoro CH 50 2-butynyl 3,4-difluoro CH» 51 2-butynyl 2-chloro CH, 52 2-butynyl 3-chloro CH, 53 2-butynyl 4-chloro CH» 54 2-butynyl 2,4-difluoro CH» 55 2-butynyl 2,5-difluoro CH, 56 2-butynyl 2,6-difluoro CH» 57 2-butynyl 3,4-difluoro CH, 58 2-butynyl 3,5-difluoro CH, 59 2-butynyl 2,3-difluoro CH; 60 2-butynyl 2-methyl CH» 61 2-butynyl 3-methyl CH» 62 2-butynyl 4-methyl CH, 63 2-butynyl 4-tert-butyl CH, 64 2-butynyl 3,5- CH, bistrifluoromethyl 65 2-butynyl Unsubstituted NH 66 2-butynyl Unsubstituted NCH; 67 2-butynyl Unsubstituted NCH,CHj 68 2-butynyl Unsubstituted NCH,OCH3; 69 2-butynyl Unsubstituted NCH;0C2Hs 70 l-methyl-2- Unsubstituted Single bond butynyl 71 l1-methyl-2- Unsubstituted Oxygen atom butynyl : 72 l-methyl-2- 2-fluoro Single bond butynyl ’ 73 4-fluoro-2- Unsubstituted Single bond butynyl
Table 1 (contd.)
Compound (R)n A
Ea SE 74 2-pentynyl 2-fluoro Single bond 75 2-pentynyl 3-fluoro Single bond 76 2-pentynyl 4-fluoro Single bond 77 2-pentynyl 2-chloro Single bond 78 2-pentynyl 3-chloro Single bond 79 2-pentynyl 4-chloro Single bond 80 2-pentynyl 2,4-difluoro Single bond 81 2-pentynyl 2,5-difluoro Single bond 82 2-pentynyl 2,6-difluoro Single bond 83 2-pentynyl 3,4-difluoro Single bond 84 2-pentynyl 3,5-difluoro Single bond 85 2-pentynyl 2,3-difluoro Single bond 86 2-pentynyl 2-methyl Single bond 87 2-pentynyl 3-methyl Single bond 88 2-pentynyl 4-methyl Single bond 89 2-pentynyl 4-tert-butyl Single bond 2-pentynyl 3,5- Single bond bistrifluoromethyl 91 2-butynyl 4-fluoro-3-methyl Single bond 92 2-butynyl 4-methyl-3-nitro Single bond 93 2-butynyl 4-methylthio Single bond 94 2-butynyl 2-methoxy Single bond 95 2-butynyl 3-methoxy Single bond 96 2-butynyl 4-methoxy Single bond 97 2-butynyl 2,3-dimethyl Single bond 198 2-butynyl 3,5-dimethyl Single bond 99 2-butynyl 2,5-dimethyl Single bond
Table 1 (contd.)
Compound (R%)n A
No. 100 2-butynyl 3,5-dibromo Single bond 101 2-butynyl 3-chloro-4-fluoro Single bond 102 2-butynyl 2,4-dichloro Single bond 103 2-butynyl 2,3~dichloro Single bond 104 2-butynyl 2,5-dichloro Single bond 105 2-butynyl 3,4-dichloro Single bond 106 2-butynyl 3,5-dichloro Single bond 107 2-butynyl 2-bromo Single bond 108 2-butynyl 3-bromo Single bond 109 2-butynyl 4-bromo Single bond 110 2-butynyl 3-nitro Single bond 111 2-butynyl 4-trifluoromethyl Single bond 112 2-butynyl 3-trifluoromethoxy [Single bond 113 2-butynyl 4-triflucromethoxy | Single bond 114 2-butynyl 3-cyano Single bond 115 2-butynyl 4-cyano Single bond 116 2-pentynyl 4-fluoro3-methyl Single bond 117 2-pentynyl 4-methyl-3-nitro Single bond 118 2-pentynyl 4-methylthio Single bond 119 2-pentynyl 2-methoxy Single bond 120 2-pentynyl 3-methoxy Single bond 121 2-pentynyl 4-methoxy Single bond 122 2-pentynyl 2,3-dimethyl Single bond 123 2-pentynyl 3,5-dimethyl Single bond 124 2-pentynyl 2,5-dimethyl Single bond 125 2-pentynyl 3, 5-dibromo Single bond
Table 1 {(contd.)
Compound (R%)n A
No. 126 2-pentynyl 3-chloro-4-fluoro Single bond 127 2-pentynyl 2,4-dichloro Single bond 128 2-pentynyl 2,3-dichloro Single bond 129 2-pentynyl 2,5-dichloro Single bond 130 2-pentynyl 3,4-dichloro Single bond 131 2-pentynyl 3,5-dichloro Single bond 132 2-pentynyl 2-bromo Single bond 133 2-pentynyl 3-bromo Single bond 134 2-pentynyl 4-bromo Single bond 135 2-pentynyl 3-nitro Single bond 136 2-pentynyl 4-trifluoromethyl Single bond 137 2-pentynyl 3-trifluoromethoxy | Single bond 138 2-pentynyl 4-trifluocromethoxy | Single bond 139 2-pentynyl 3-cyano Single bond 140 2-pentynyl 4-cyano Single bond
Examples of the harmful arthropod against which the compound of the present invention exhibits controlling effect are insects and mites, specifically, following ones.
Hemiptera insect pest: planthoppers such as small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens) and white-backed rice planthopper (Sogatella furcifera), leafhoppers such as green rice leafhopper (Nephotettix cincticeps)and tea green leafhopper (Empoasca onukii), aphids such as cotton aphid (Aphis gossypii) and green peach aphid (Myzus persicae), stink bugs, whiteflies such as greenhouse whitefly (Trialeurodes vaporariorum), sweet-potato whitefy (Bemisia tabaci) and silverleaf whitefly (Bemisia argentifolii),
scales, lace bugs, jumping plantlice, etc.
Lepidoptera insect pest: pyralid moths such as rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), European corn borer (Ostrinia nubilalis) and bluegrass webworm (Parapediasia teterrella), owlet moths such as tabaco cutworm (Spodoptera litura),
Spodoptera exigua, rice armyworm (Pseudaletia separata), cabbage armyworm (Mamestra brassicae), black cutworm (Agrotis ipsilon), Trichoplusia spp., Heliothis spp.,
Helicoverpa spp. and Earias spp., whites and sulfer butterflies such as common cabbage worm (Pieris rapae crucivora), tortricid moths such as Adoxophyes orana fasciata, Grapholita molesta and codling moth (Cydia pomonella), Carposinidae such as peach fruit moth (Carposina niponensis), Bucculatricidae such as Lyonetia clerkella, leaf-blotch miners such as Phyllonorycter ringoniella, Phyllochistinae such as Phyllocnistis citrella,
Yponomeutidae such as diamondback moth (Plutela xylostella), gelechid moths such as pink ball worm (Pectinophora gossypiella), Arctiidae, clothes moths, etc.
Diptera insect pest: mosquitos such as common mosquito (Culex pipiens pallens), oriental latrine fly (Culex tritaeniorhynchus) and southern house mosquito {Culex guinguefasciatus), Aedes spp. such as Aedes aegypti and
Aedes albopictus, Anophles spp. such as Anopheles sinensis,
midges, house flies such as housefly (Musca domestica) and false stablefly (Muscina stabulans), Calliphoridae,
Sarcophagidae, little housefly, Anthomyiidae such as seedcrn maggot (Delia platura) and onion maggot (Delia antiqua), fruit flies, small fruit flies, moth flies, black flies, Tabanidae, stable flies , leafminer flies, etc.
Coleoptera insect pest: corn rootworm such as western corn rootworm {(Diabrotica virgifera virgifera) and southern corn rootworm (Diabrotica undecimpunctata howardi), scarabs such as cupreous chafer (Anomala cuprea) and soybean beetle (Anomala rufocuprea), weevils such as maize weevil (Sitophilus zeamais), ricewater weevil (Lissorhoptrus oryzophilus) and adzuki bean weevil (Callosobruchuys chienensis), darkling beetles such as yellow mealworm (Tenebrio molitor) and red flour beetles (Tribolium castaneum), leaf beetles such as Oulema oryzae, cucurbit leaf beetle (Aulacophora femoralis), striped flea beetle (Phyllotreta striolata) and Colorado beetle (Leptinotarsa decemlineata), Anbiidae , Epilachna spp. such as twenty- eight-spotted ladbirds (Epilachna vigintioctopunctata), powderpost beetles, false powderpost beetles, long-horned beetles, Paederus fuscipes, etc.
Thysanoptera insect pest: thrips such as Thrips spp. such as Thrips palmi, Frankliniella spp. such as western flower thrips (Frankliniella occidentalis), Sciltothrips ssp. such as yellow tea thrips (Sciltothrips dorsalis),
Plaeothripidae, etc.
Hymenoptera insect pest: saufliws, ants, hornets, etc.
Dictyoptera insect pest: cockroachs, German cockroachs, etc.
Orthoptera insect pest: glasshoppers, mole crickets, etc.
Siphonaptera insect pest: feas, etc.
Anoplura insect pest: human body louse, etc.
Isoptera insect pest: termites, etc.
Acarina insect pest: spider mites etc.
The compound of the present invention has characteristic in controlling effect against Hemiptera insect pests, Lepidopterta insect pests, Coleoptera insect pests and Thysanoptera insect pest.
The harmful arthropod controlling composition of the present invention may be the compound of the present invention itself. Usually, the compound of the present invention and, for example, a solid carrier, a liquid carrier, a gaseous carrier and/or a bait (base material for poison bait) are mixed, a surfactant and other adjuvants for formulation are added if necessary, and they are formulated into, for example, oils, emulsions, flowables, granules, powders, poison baits or microcapsules to obtain the harmful arthropod controlling composition of the present invention. The formulation usually contains 0.01 to 95% by weight of the compound of the present invention.
Examples of the solid carrier used for formulation into the composition include fine powders or particles such as clays (kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay etc.), talc, ceramics, other inorganic minerals (sericite, quarts, sulfur, active carbon, calcium carbonate, hydrated silica etc.), and chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.). Examples of the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N,N-dimethyl formamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane carbon tetrachloride, etc.), dimethyl sulfoxide, and vegetable oils (soybean oil, cottonseed oil, etc.), and examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas. Examples of a surfactant include alkyl sulfate salts, alkyl sulfonic acid salts, alkylaryl sulfonic acid salts, alkylaryl ethers and their polyoxyethylene derivatives, polyethylene glycols ethers, polyhydric alcohol esters and sugar alcohol derivatives.
Examples of adjuvants for formulation include sticker, dispersants and stabilizers, specifically, casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivative, alginic acid etc.), lignin derivative, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), PAP (acidic isopropyl phosphate), BHT (2,6-di-tert- butyl-4-methylphenol), BHA (mixture of 2-tert-butyl-4- methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid and fatty acid ester.
Examples of the base of a poison bait include a bait ingredient such as cereal powder, vegetable oil, sugar and crystalline cellulose, and antioxidant such as dibutylhydroxytoluene and nordihydroguaialetic acid, preservative such as dehydroacetic acid, agent for preventing erroneous eating by children or pets such as red pepper powder, and insect pest attracting perfume such as cheese perfume, onion perfume, and peanuts oil.
The harmful arthropod controlling composition of the present invention is used by applying to harmful arthropods or a place where harmful arthropods inhibit. For example,
when a harmful arthropod parasitizing a cultivating plant is controlled, the arthropod can be controlled by scattering the harmful arthropod controlling composition of the present invention on a ground part of the cultivating plant, or by pouring the harmful arthropod controeclling composition of the present invention over a root part of the cultivating plant.
When the harmful arthropod controlling composition of the present invention is used, the application amount is usually 0.1 to 1,000 g per 1,000 m? in terms of the compound of the present invention. Emulsions, wettable powders, flowables and microcapsules are usually applied by diluting with water so that the active ingredient concentration becomes 10 to 10,000 ppm, and granules and powders are usually applied as they are.
Alternatively, the harmful arthropod controlling composition of the present invention can be used together with other insecticide, nematicide, acaricide, fungicide, herbicide, plant growth regulating agent, synergist, fertilizer, soil conditioner, animal feed, etc.
Examples of such insecticide, acaricide and nematicide include organophosphorous compounds such as fenitrothion, fenthion, pyridafenthion, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, methidathion, disulfoton,
DDVP, sulprofos, profenofos, cyanophos, dioxabenzofos,
Claims (9)
1. A 1,2,4-thiadiazole compound represented by the formula (1): N—S A rlo— 3 we. (1) N A wherein R' represents a C3-C7 alkynyl group optionally substituted with one or more halogen atom(s), R? represents a halogen atom, a Cl-C4 alkyl group, a Cl-C4 haloalkyl group, a Cl-C4 alkoxy group, a Cl1-C4 haloalkoxy group, a Cl-C4 alkylthio group, a cyano group or a nitro group, n represents an integer of 0 to 5, provided that, when n represents an integer of 2 or more, respective R’s may be the same or different, A represents an oxygen atom, a sulfur atom, a single bond, a CR’R* group Or a NR® group, R® and R* represent each independently a hydrogen atom or a Cl-C4 alkyl group, and R® represents a hydrogen atom, a Cl-C7 alkyl group, a C1-C3 haloalkyl group, a C2-C4 (alkoxyalkyl) group, a C2- C4 (halocalkoxyalkyl) group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C7 alkynyl group, a C3-C7 haloalkynyl group or a cyanomethyl group.
2. The 1,2,4-thiadiazole compound according to claim 1, wherein A in the formula (1) is a single bond.
3. The 1,2,4-thiadiazole compound according to claim
1 or 2, wherein R! in the formula (1) is a 2-propynyl group, a 2-butynyl group or 2-pentynyl group. 4, The 1,2,4-thiadiazole compound according to claim 1l or 2, wherein R! in the formula (1) is a 2-butynyl group or a 2-pentynyl group.
5. A composition for controlling a harmful arthropod which comprises an effective amount of the 1,2,4- thiadiazole compound according to claim 1.
6. A method for controlling a harmful arthropod which comprises applying, to harmful arthropods or a place where harmful arthropods inhabit, a 1,2,4-thiadiazole compound represented by the formula (1): N—S NX rRlo—{ 3 oe (1) N A wherein R! represents a C3-C7 alkynyl group optionally substituted with one or more halogen atom(s), R? represents a halogen atom, a Cl-C4 alkyl group, a Cl-C4 haloalkyl group, a Cl1-C4 alkoxy group, a Cl1-C4 haloalkoxy group, a C1-C4 alkylthio group, a cyano group or a nitro group, n represents an integer of 0 to 5, provided that, when n represents an integer of 2 or more, respective R’s may be the same or different, A represents an oxygen atom, a sulfur atom, a single bond, a CR’R* group or a NR® group, R® and R? represent each independently a hydrogen atom or Cl-C4 alkyl group, and R® represents a hydrogen atom, a Cl1-C7 alkyl group, a Cl1-C3 haloalkyl group, a C2-C4 (alkoxyalkyl) group, a C2- C4 (haloalkoxyalkyl) group, a C3-C6 alkenyl group, a C3-Cb haloalkenyl group, a C3-C7 alkynyl group, a C3-C7 haloalkynyl group or a cyanomethyl group.
7. The controlling method according to claim 6, wherein the harmful arthropod is a Hemiptera insect pest, a Lepidoptera insect pest, a Coleoptera insect pest or a Thysanoptera insect pest.
8. The controlling method according to claim 6, wherein the harmful arthropod is a Hemiptera insect pest or a Thysanoptera insect pest.
9. Use of the 1,2,4-thiadiazole compound according to claim 1 as an active ingredient of a composition for controlling a harmful arthropod.
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2005
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