MXPA99002967A - Insecticide/miticide composition - Google Patents
Insecticide/miticide compositionInfo
- Publication number
- MXPA99002967A MXPA99002967A MXPA/A/1999/002967A MX9902967A MXPA99002967A MX PA99002967 A MXPA99002967 A MX PA99002967A MX 9902967 A MX9902967 A MX 9902967A MX PA99002967 A MXPA99002967 A MX PA99002967A
- Authority
- MX
- Mexico
- Prior art keywords
- phenoxybenzyl
- dimethylcyclopropanecarboxylate
- insecticidal
- enyl
- cyano
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 62
- 239000002917 insecticide Substances 0.000 title abstract description 14
- 239000000642 acaricide Substances 0.000 title abstract description 5
- 239000004615 ingredient Substances 0.000 claims abstract description 33
- 239000002728 pyrethroid Substances 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims abstract description 15
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000000749 insecticidal effect Effects 0.000 claims description 53
- 230000000895 acaricidal effect Effects 0.000 claims description 40
- -1 2-Methylbiphenyl-3-ylmethyl Chemical group 0.000 claims description 19
- 241000607479 Yersinia pestis Species 0.000 claims description 16
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 12
- 239000005946 Cypermethrin Substances 0.000 claims description 9
- 229960005424 cypermethrin Drugs 0.000 claims description 9
- 239000005874 Bifenthrin Substances 0.000 claims description 8
- 239000005896 Etofenprox Substances 0.000 claims description 8
- INISTDXBRIBGOC-CGAIIQECSA-N [cyano-(3-phenoxyphenyl)methyl] (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate Chemical compound N([C@@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-CGAIIQECSA-N 0.000 claims description 8
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims description 8
- 229950005085 etofenprox Drugs 0.000 claims description 8
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 8
- 229960000490 permethrin Drugs 0.000 claims description 8
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims description 7
- VMORCWYWLVLMDG-YZGWKJHDSA-N Pyrethrin-II Natural products CC(=O)OC(=C[C@@H]1[C@H](C(=O)O[C@H]2CC(=O)C(=C2C)CC=CC=C)C1(C)C)C VMORCWYWLVLMDG-YZGWKJHDSA-N 0.000 claims description 7
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 claims description 7
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 claims description 7
- 240000004460 Tanacetum coccineum Species 0.000 claims description 6
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 claims description 6
- 229940015367 pyrethrum Drugs 0.000 claims description 6
- 230000003129 miticidal effect Effects 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims 2
- 241000238876 Acari Species 0.000 abstract description 8
- 241000238631 Hexapoda Species 0.000 abstract description 3
- 229940126062 Compound A Drugs 0.000 description 34
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 34
- 239000000126 substance Substances 0.000 description 22
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- 231100000111 LD50 Toxicity 0.000 description 8
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- WIFXJBMOTMKRMM-UHFFFAOYSA-N halfenprox Chemical compound C=1C=C(OC(F)(F)Br)C=CC=1C(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 WIFXJBMOTMKRMM-UHFFFAOYSA-N 0.000 description 4
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- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 229960001591 cyfluthrin Drugs 0.000 description 3
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 3
- 235000014666 liquid concentrate Nutrition 0.000 description 3
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
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- ZRYXMBWYACLLRH-JTQLQIEISA-N (2s)-2-[4-(difluoromethoxy)phenyl]-3-methylbutanoic acid Chemical compound CC(C)[C@H](C(O)=O)C1=CC=C(OC(F)F)C=C1 ZRYXMBWYACLLRH-JTQLQIEISA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 239000004563 wettable powder Substances 0.000 description 2
- VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 description 1
- UIWNHGWOYRFCSF-UHFFFAOYSA-N 3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound COC(=O)C(C)=CC1C(C(O)=O)C1(C)C UIWNHGWOYRFCSF-UHFFFAOYSA-N 0.000 description 1
- SPVZAYWHHVLPBN-HYXAFXHYSA-N 3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(O)=O SPVZAYWHHVLPBN-HYXAFXHYSA-N 0.000 description 1
- QLMFPUPRPMLSCX-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(2-ethoxyethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound BrC1=C(C(F)(F)F)N(CCOCC)C(C=2C=CC(Cl)=CC=2)=C1C#N QLMFPUPRPMLSCX-UHFFFAOYSA-N 0.000 description 1
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- 241001159389 Aculops pelekassi Species 0.000 description 1
- 241001347514 Carposinidae Species 0.000 description 1
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- 241001414720 Cicadellidae Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
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- 229920000742 Cotton Polymers 0.000 description 1
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- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
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- 241001190778 Lyonetiidae Species 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
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- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
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Abstract
An insecticide/miticide composition characterized by containing 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile and a pyrethroid insecticide ingredient as the active ingredients. This composition is effective against harmful insects and ticks resistant to commercially available insecticide/miticides.
Description
COMPOSITION INSECTICIDAACARICIDA
FIELD OF THE INVENTION
This invention relates to insecticidal and acaricidal compositions characterized in that 4-bromo-2- (4-chlorophenyl) -1- (ethoxyethyl) -5- (trifluoromethyl) pyrrole-3-carbonitrile (hereinafter referred to as Compound A) is mixed. and natural pyrethroid insecticidal ingredients and / or synthetic pyrethroid insecticidal ingredients. The insecticidal and acaricidal compositions of the invention can be effectively applied in the agro-horticultural field.
ANTECEDENTS OF THE TECHNIQUE
Compound A, which is an active ingredient of the insecticidal and miticidal composition of the invention, is an insecticidal and acaricidal agent against agro-horticultural pests and is known to be effective against insects such as pests such as pests of H e m p t e r a t a l as s a l t a r i l a
(Doltocephalidae), lepromatoptera pests such as the diamond back moth (Plutella xylostella), common nocturnal caterpillar (Spodoptera litura), and apple leafminer
(Phyllonorycter ringoniella), and plague of Thysanoptera such as Thrips of the palm and Thrips of the yellow tea (Spirtothrips REF: 29793
dorsalis) and agrohorticultural pests such as mites such as the spider mite (Tetranychus urticae koch), the spider mite or Kanzawa (Tetranychus kanzawai kishida) and Aculops pel e-kassi. The second active ingredient of the insecticidal and miticidal composition of the invention is a pyrethroid insecticidal ingredient, of which the following compounds are representative: As a known natural pyrethroid insecticidal ingredient, the extracted pyrethrum ingredient, a mixture containing (Z) - ( S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (IR) -trans-2, 2-dimethyl-3- (2-methylprop-1-enyl) Cyclopropane carboxylate (Pyrethrin I) and (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (E) - (IR) -trans-3 (2-methoxycarbonylprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate (Pyrethrin II) and the like are mentioned. As synthetic insecticidal pyrethroid ingredients, 2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether (Etofenprox), (RS) -a-cyano-3-phenoxybenzyl (Z) - (1RS, 3RS) -3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate (Cihalothrin),
(RS) -α-cyano-4-fluoro-3-phenoxybenzyl (1RS, 3RS; 1RS, 3SR) -3- (2, 2 -di chloro vinyl) -2,2-dimethylcyclopropanecarboxylate (Ciflutrin), (RS) - a-cyano-3-f-enoxybenzyl (1RS, 3RS; 1RS, 3SR) -3- (2, 2-dichlorovinyl) -2, 2-dimethylcyclopropanecarboxylate (Cypermethrin),
4 - . 4-ethoxyphenyl [3- (4-fluoro-3-phenoxyphenyl) propyl] dimethylsilane (Silaf luphene), (S) -a-cyano-3-phenoxybenzyl (1RS, 3S) -2, 2-dimethyl-3- [( RS) 1,2,2,2-tetrabromoethyl] cyclopropanecarboxylate (Tralometrine), 2- (4-bromodifluoromethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether (Halfenprox), 2-methylbiphenyl-3-ylmethyl (Z) - ( 1RS, 3RS) -3- (2-chloro-3, 3, 3-trifluoroprop-l-enyl) -2, 2-dimethylcyclopropanecarboxylate (Bifenthrin), (RS) -a-cyano-3-phenoxybenzyl-2, 2, 3, 3- trame ti 1-cyclopropanecarboxylate (Fenpropatrine), (RS) -a-cyano-3-phenoxybenzyl (RS) -2- (4-chlorofenyl) -3-methylbutyrate (Fenvalerate), (RS) - a -cyano- 3- f enoxybenzyl (S) -2- (4-difluoromethoxy-phenyl) -3-methylbutyrate (Flucitrinate), (RS) -a-cyano-3-f-enoxybenzyl N- (2-chloro-a, a, a, trifluoro-p-tolyl) -D-valinate (Fluvalinate), 3-phenoxybenzyl (1RS, 3RS, 1RS, 3RS) -3- (2, 2 -di chlorovinyl) -2, 2-
dimethylcyclopropancarboxylate (Permethrin) and the like are mentioned. Of the compounds mentioned above, they are known to be effective against agrohorticultural pests such as insects such as Hemiptera, Lepidoptera and Coleoptera insects or mites. Hitherto, acaricidal insecticidal agents have been developed in order to control various pests such as agro-horticultural pests or hygienic pests and have been used in practice alone or in mixtures. Nevertheless, pests which have acquired resistance against various agents have been appearing as a result of the repeated use of these agents. In particular, spider mites (Tetranychidae) are prone to easily develop resistance against pesticide agents due to their ability to deposit large quantities of eggs and produce large quantities of generations which, in themselves, require only a few days for their development , have a high rate of mutation and frequent endogamous growth, due to minimal migration. For these reasons, the two-spot spider mite
. { Tetranychus urticae koch), Kanzawa spider mite (Tetranychus kanzawai kishida), Aculops pelekassi, and the like have acquired resistance, to some extent, against almost all existing plagiarism agents.
Therefore, in order to avoid and control the damage caused by spider mites, the development of an insecticidal and acaricidal agent which shows an elevated effect against spider mites which have acquired resistance against conventional acaricidal agents is highly desirable. However, to invent an insecticidal and acaricidal composition which does not show cross-resistance with existing insecticidal and acaricidal agents, which do not present problems of toxicity and which has little negative impact on the environment, is extremely difficult. In addition, a period of almost 10 years is required for the development of an invention. Therefore, in order to apply an effective agent for a long time, the rotational application of agents with different mechanisms of action for a good practice of pest control has been adopted. However, this approach does not necessarily provide satisfactory results. After a resistance problem has arisen, a countermeasure for resistance has been studied using a combination of insecticidal and acaricidal agents. However, a high synergistic action has not always been found. On the other hand, compound A, which is an active ingredient of the insecticidal and acaricidal composition of the invention, has reached the market very
recently and shows a high acaricidal effect now even when used alone. However, from the background of resistance problems of almost all acaricidal agents in the past, it is likely that a similar problem may arise with compound A, too. The object of this invention is to provide an acaricide composition which demonstrates a high level of control against spider mites which has an acquired resistance against compound A.
DESCRIPTION OF THE INVENTION
In order to provide a countermeasure to the problem of spider resistance against compound A before such a problem occurs, the synergistic action was studied with existing insecticidal, acaricidal and fungicidal agents using resistant species which have been artificially established in the laboratory when selecting spider mites which have been treated with compound A. Therefore, it has now been found that a composition which contains compound A in combination with pyrethroid insecticidal ingredients demonstrates a synergistic joint effect which can not be
anticipated from each individual ingredient, and is very effective as an insecticidal and acaricidal composition, resulting in the obtention of this invention. Therefore, the main point of the present invention resides in insecticidal and acaricidal compositions characterized in that 4-bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) pyrrole-3-carbonitrile (Compound A ). The representative spider mites controlled by the present invention are: two-spot spider mite (Tetranychus urticae koch), Tetranychus cinnabarinus (Boisduval), Kanzawa spider mite (Tetranychus Kanzawaikishida), hawthorn spider mite (Tetranychus viennensiszacher) and the like. Advantageously, the insecticidal and acaricidal composition of the invention show not only a synergistic acaricidal appearance against the aforementioned spider mites, but also demonstrate simultaneous control of problematic pests of fruit trees, for example citrus fruits, apples and pears such as odorata moths. the leaves (Tortri cidae), the leafminer moths Carposinidae
(Lyonetii dae), plant bugs (Pentatomi dae), aphids
(Aphi didae), jumping (Del tociphalidae) and thrips
(Thripidae); on tea plants such as leafhoppers, aphids and Thrips; about vegetables such as
diamond back moths (Pl utella xylostella), Mamestra brassicae, leaf weevils (Chrysomelidae), aphids, white flies (Al eyrodidae), thrips and the like. Compound A, which is an active ingredient of the insecticidal and acaricidal composition of the invention, is a known compound described in Japanese Patent Laid-Open Publication (Kokai) No. 104042/89, and its method of use as an agent insecticide and acaricide agrohorticultural is also shown in the publication. It can be synthesized according to the method described therein. On the other hand, many compounds are known as pyrethroid insecticidal ingredients, the second active ingredient of the insecticidal and acaricidal composition of the invention. Below are their generic names and chemical names. However, these examples are not intended to limit the scope of the invention.
Generic name: Pyrethrin I Chemical name: (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (IR) -trans-2, 2- dimethyl-3- (2-methylprop-1-enyl) -cyclopropanecarboxylate.
Generic name: Pyrethrin II Chemical name: (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (E) - (IR) -transfer 3- (2-Methyloxycarbonylprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate
Generic name: Etofenprox Chemical name: 2- (4-ethoxy-enyl) -2-methylpropyl-3-f-enoxybenzyl ether.
Generic name: Cihalotrina Chemical Name: (RS) -a-cyano-3-phenoxybenzyl (Z) - (1RS, 3RS) -3- (2-c l o r o - 3, 3, 3 - t r i f l u o r o p r o p e n i l) -2,2-dimethylcyclopropanecarboxylate.
Generic name: Cyfluthrin Chemical Name: (RS) - «-ciano-4-f luoro-3-phenoxybenzyl (lRS, 3RS; lRS, 3SR) -3- (2, 2 -di chloro vinyl) -2,2-dimethylcyclopropanecarboxylate .
Generic name: Cypermethrin Chemical Name: (RS) -acyano-3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2, 2 -di chloro vinyl) -2, 2-dimethylcyclopropanecarboxylate.
Generic name: Silafluofen Chemical name: 4-e t oxi f eni 1 [3 - (4-f luo r o -3-phenoxyphenyl) propyl] dimethylsilane.
Generic name: Silafluofen Chemical name: 4-ethoxyphenyl [3- (4-f luoro-3-phenoxyphenyl) propyl] -di-ethylsilane.
Generic name: Tralometrine Chemical name: (S) -acyano-3-phenoxybenzyl (1RS, 3S) -2, 2-dimethyl-3- [(RS) 1,2,2,2-tetrabromoethyl] cyclopropanecarboxylate.
Generic name: Halfenprox Chemical name: 2- (4-bromodifluoromethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether.
Generic name: Bifenthrin Chemical Name: 2-methylbiphenyl-3-ylmethyl (Z) - (1RS, 3RS) -3- (2-chloro-3, 3, 3-trifl uo rop rop -l - en il) - 2 , 2-dimethylcyclopropanecarboxylate.
Generic name: Fenpropathrin Chemical name: (RS) -a-cyano-3-phenoxybenzyl-2,2,3,3-tetramethyl-cyclopropanecarboxylate.
Generic name: Fenvalerate Chemical Name: (RS) -acyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate.
Generic name: Flucitrinate Chemical name: (RS) -a-cyano-3-phenoxybenzyl (S) -2- (4-difluoromethoxyphenyl) -3-methylbutyrate.
Generic name: Fluvalinate Chemical Name: (RS) -acyano-3-phenoxybenzyl N- (2-chloro-a, a, a, a-trifluoro-p-tolyl) -D-valinate.
Generic name: Permethrin Chemical name: 3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2, 2-dichloroxy) -2, 2-dimethylcyclopropanecarboxylate.
The names mentioned before the insecticide agents are generic names described in "Agrochemicals Handbook 1992 Edition" (published July 30, 1992 by the Plant Protection Association of Japan) and "SHIBUYA INDEX-1996- (7th Edition)" ( published on April 1, 1996 by ZENNOH). In this invention, among those mentioned above, especially the extracted pyrethrum ingredient containing Pyrethrin I and Pyrethrin II, Etofenprox, Cihalotrine,
Cyfluthrin, Cypermethrin, Bifenthrin, Fenpropathrin, Fluvalinate, Permethrin and the like are preferable due to their high synergistic action with 4-bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) pyrrole-3-. carbonitrile (compound A). The insecticidal and acaricidal composition of the invention can be formulated as a wettable powder, an aqueous concentrate, emulsion, liquid concentrate, sol (flowable agent), powder, aerosol or the like by conventional methods such as mixing compound A and the pyrethroid insecticidal ingredient or ingredients with a suitable carrier and auxiliary materials, such as emulsifiers, dispersants , stabilizers, agents that improve suspension, penetrants and the like. The weights (%) of the insecticidal active ingredients of the composition of the invention in the formulations mentioned above are preferably in the range of about 1-901 for wettable powders, aqueous concentrates, emulsions, liquid concentrates and formulations in sol, 0.5-10 % for powder formulations and 0.01-2% for aerosol formulations. Suitable carriers for use in the invention can be any solid or liquid carrier which is commonly used for an agrohorticultural composition and is not limited to specific substances. In the formulations
They can use various surfactants, stabilizers or other auxiliary ingredients, as needed. The insecticidal and acaricidal composition of the invention may also be present in commercially useful formulations or in application forms prepared from these formulations as a mixture with other active compounds, for example various insecticidal, acaricidal, fungicidal and herbicidal agents, growth regulators. of plants, repellents, attractants, synergists and fertilizers and fragrances, in order to expand the applicability of the insecticidal and acaricidal composition of the invention. The mixing ratio of compound A and the active ingredient of known peritroidal insecticidal agents are generally as follows. The ratio of the latter to one part by weight of the first is generally 0.01-100 parts by weight, and preferably 0.5> 0.05. -20 parts by weight. The method of application of the insecticidal and acaricidal composition of the invention is as follows. Although the amount of application may differ according to the amounts of pests or mites and the classes and forms of cultivation of the target crop, the amount of active ingredients (total amount of compound A and the active ingredient of the known peritroid insecticidal agents) it is generally 0.1-1000 g and preferably 40-500 g per 10 acres. If
of wettable powders, aqueous concentrates, emulsions, liquid concentrates and sols, can be diluted with water and applied to the crop at an application rate of 100-700 liters per 10 acres. In the case of powders or aerosols, the crop can be treated with the undiluted formulation.
EXAMPLES OF THE INVENTION
The insecticidal and acaricidal composition of the invention is illustrated by the examples set forth below. These examples are not intended to limit the active ingredients and their formulation proportions, auxiliary ingredients and their aggregate amounts and the like. In the examples, the parts mean parts by weight.
EXAMPLE OF FORMULATION 1 (EMULSION).
^ available from Toho Chemical Industry Ltd.
An emulsion is obtained by mixing homogeneously and dissolving the aforementioned ingredients.
EXAMPLE OF FORMULATION 2 (HUMECTABLE DUST)
** available from Shionogi & Co. Ltd. *** available from Zeeklite Ind. Available from Toho Chemical Industry Ltd.
A wettable powder is obtained by homogeneously mixing the aforementioned ingredients in an air jet mill.
EXAMPLE OF FORMULATION 3 (FLUENT AGENT)
***** available from Toho Chemical Ind. Co., Ltd.
Compound A, Cypermethrin and ethylene glycol previously mixed, Sorpol AC3020 and xanthan gum are mixed well in water and dispersed to obtain a suspension. This suspension is then wet pulverized by Dynomill (Shinmaru Enterprises) to obtain a flowable agent.
EXAMPLE OF FORMULATION 4 (POWDER)
The ingredients mentioned above are mixed homogeneously and pulverized to obtain powder.
EXAMPLE OF FORMULATION 5 (AEROSOL)
The ingredients mentioned above are mixed, dissolved and filled into an aerosol container, and after joining a valve part, 60 parts of propellant (LPG / DME mixed gas) are pressed through the valve part to obtain a spray. The effectiveness and usefulness of the insecticidal and acaricidal composition of the invention is demonstrated by the following test example.
EXAMPLE OF TEST 1
The test for the acaricidal effect against female images (adults) of Kansawa spider mites (Tetranychus kanzawai ki shida) which are resistant to compound A. Round leaf discs (2 cm diameter) are cut from a first leaf of kidney bean when using a sheet punch and four sheet sheets are placed on wet sanitary cotton in a 8 cm diameter PVC container. Each leaf disc is inoculated with four female Kanzawa spider (Tetranychus kanzawai ki shida) which has acquired a strong resistance to compound A. After inoculation, the insecticidal and acaricidal composition of the invention, compound A and pyrethroid insecticidal agent or agents are dispersed in water containing 200 ppm of a diluent (Sorpol 3005X, manufactured by Toho Chemical Industry Ltd.) and are diluted so as to obtain the predetermined concentration of active ingredient. Each PVC container is sprayed with 3.5 ml of the test solution by using a rotating spray tower
(manufactured by Mizuho Scientific Co., Ltd.) and stored in a constant temperature chamber maintained at 25 + ° C
(32 individuals are tested by concentration, 4-5 concentrations are evaluated per formulation and two operations are repeated). Two days after the treatment,
investigated the number of live and dead female Kansawa spider mite (Tetranychus kanzawai kishida) on the leaf disk and mortality (%) was calculated according to the formula shown below. From these mortality data, the LC50 values are obtained by the conventional probit method.
Mortality (%) = Number of dead mites X 100 Number of live mites + number of dead mites
In addition, the coefficient of co-toxicity was calculated by applying the formula of Sun and Johnson (J. Econ. Ent., Vol. 53, p.887, 1960) which is generally used to determine the degree of synergistic activity. The LC50 value of each individual active ingredient, which constitutes the insecticidal and miticidal composition of the invention, is shown in Table I. The LC50 values and co-toxicity coefficients calculated by the Sun and Johnson formula mentioned below of the composition of the invention are shown in Table II.
Co-toxicity coefficient = actual toxicity index of the mixture X 100 theoretical toxicity index of the mixture
For the values mentioned above greater than 100, a larger value indicates a stronger synergistic action. For a value equal to 100, an additive action is indicated. For values less than 100, the smaller value indicates a larger antagonistic action. A more detailed description of the calculation of the co-toxicity coefficient of the Sun and Johnson method mentioned above is as follows. Each LC5n value of test compound A and test compound B is determined and the LC50 value of the mixture thereof is determined.
actual toxicity index of the mixture M = LC50 of the test compound A X 100 LC5n of the mixture M
theoretical toxicity index of the mixture M = (toxicity index of compound A of test X proportion of compound A of test in mixture M (%) + toxicity index of compound B of test X proportion of compound B of test in the mixture M (%)) X 100. With the proviso that the toxicity indices of test compound A and test compound B are the following:
toxicity index of test compound A = 100 toxicity index of test compound B = LC50 of test compound A X 100 LC50 of test compound B
TABLE I
Effect of compound A and pyrethroid insecticidal agents against female Kanzawa spider that have acquired resistance against compound A.
The acaricidal effect of each compound is tested by using females from a colony resistant to compound A which is obtained by a prolonged artificial selection procedure with compound A in a laboratory in a colony of Kanzawa spiders which have been collected in the countryside. The effect of compound A is 1500 ppm as the LC5C value. Since the effect of compound A against the susceptible strains of spider mites, which is not mentioned in the Table, is about 5 ppm as LC50 value, this strain developed with approximately 300 times resistance against compound A. Since this Kanzawa spider comes from a colony which has acquired resistance against the pyrethroid insecticide agents already at the time of harvesting in the field, all tested pyrethroid insecticidal agents show only low effects.
Table II
Effect and synergistic action of the insecticidal and acaricidal composition of the invention against Kanzawa spider females which have acquired resistance against compound A.
Since the coefficients of co-toxicity of the insecticidal and miticidal compositions of the invention all have values that exceed by much to 100, it is considered that in the test example a strong synergistic action of Compound A and Etofenprox, Cihalotrine, has been demonstrated, Cyfluthrin, Cypermethrin, Piretrum, Bifenthrin, Fenpropathrin, Fluvalinate or Permethrin.
INDUSTRIAL APPLICABILITY
The present invention provides effective insecticidal and acaricidal agents against pests and mites, the
which are resistant against insecticidal and acaricidal agents currently on the market. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is the conventional one for the manufacture of the objects or products to which it refers.
Claims (8)
1. An insecticidal and acaricidal composition characterized in that it comprises as active ingredients 4-bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) pyrrole-3-carbonitrile and a pyrethroid insecticidal ingredient or ingredients.
2. The insecticidal and acaricidal composition according to claim 1, characterized in that it contains 0.1-5 parts by weight of a pyrethroid insecticidal ingredient or ingredients with respect to one part by weight of 4-bromo-2- (4-chlorophenyl) -1. - (ethoxymethyl) -5- (trifluoromethyl) pyrrole-3-carbonitrile.
3. The insecticidal and acaricidal composition according to claim 1, characterized in that the pyrethroid insecticidal ingredients are selected from the group consisting of the following (1) - (9): (1) extract extracted from pyrethrum containing (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (IR) -trans-2, 2-dimethyl-3- (2-meth i lprop) - 1-enyl) cyclopropanecarboxylate (Pyrethrin I) and (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (E) - (IR) -trans-3- (2- methoxycarbonylprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate (Pyrethrin II); (2) 2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether (Etofenprox); (3) (RS) -acyano-3-phenoxybenzyl (Z) - (1RS, 3RS) -3- (2-c l o r o - 3, 3, 3 - t r i f l u o r o p r o p e n i l) -2,2-dimethylcyclopropanecarboxylate (Cihalothrin); (4) (R S) - a - c i a n o - 4 - f l u or r o - 3 -f-enoxybenzyl (1RS, 3RS; 1RS, 3SR) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (Ciflutrin); (5) (RS) -a-cyano-3-phenoxybenzyl (1RS, 3RS; 1RS, 3SR) -3- (2, 2-dichlorovinyl) -2, 2-dimethylcyclopropanecarboxylate (Cypermethrin); (6) 2-Methylbiphenyl-3-ylmethyl (Z) - (1RS, 3RS) -3- (2-chloro-3, 3, 3- t ri f luo roprop- 1 - eni l) - 2, 2 - dimethylcyclopropanecarboxylate (Bifenthrin); (7) (RS) -o-cyano-3-phenoxybenzyl-2, 2,3,3-tetramethyl-cyclopropanecarboxylate (Fenpropatrine); (8) (RS) -acyano-3-phenoxybenzyl N- (2-chloro-a, a, a, a-trifluoro-p-tolyl) -D-valinate (Fluvalinate); and (9) 3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (Permethrin).
4. The insecticidal and acaricidal composition according to claim 2, characterized in that the pyrethroid insecticidal ingredients are selected from the group consisting of the following (l) - (9): (1) ingredient extracted from pyrethrum containing (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (IR) -trans-2, 2-dimethyl-3- (2-methyl) lpropyl-inyl) cyclopropanecarboxylate (Pyrethrin I) and (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (E) - (IR ) -trans-3- (2-methoxycarbonylprop-1-enyl) -2, 2-dimethylcyclopropanecarboxylate (Pyrethrin II); (2) 2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether (Etofenprox); (3) (RS) -acyano-3-phenoxybenzyl (Z) - (1R ?, 3RS) -3- (2-c l o r o - 3, 3, 3-t r i f l u o r o p r o p e n i l) -2,2-dimethylcyclopropanecarboxylate (Cihalothrin); (4) (R S) - a - c i a n o - 4 - f l u or r o - 3 -f-enoxybenzyl (1RS, 3RS; 1RS, 3SR) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (Ciflutrin); (5) (RS) -a-cyano-3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2, 2-dichlorovinyl) -2, 2-dimethylcyclopropanecarboxylate (Cypermethrin); (6) 2-Methylbiphenyl-3-ylmethyl (Z) - (1RS, 3RS) -3- (2-cl-3, 3, 3-t ri f luoropro-1-eni I) - 2, 2 - dimethylcyclopropanecarboxylate (Bifenthrin); (7) (RS) -a-cyano-3-phenoxybenzyl-2, 2,3,3-tetramethyl-cyclopropanecarboxylate (Fenpropatrine); (8) (RS) -acyano-3-phenoxybenzyl N- (2-chloro-a, a, a, a-trifluoro-p-tolyl) -D-valinate (Fluvalinate); and (9) 3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2, 2-dichlorovinyl) -2,2-dimethylcyclopentanecarboxylate (Permethrin).
5. A method for controlling insecticidal and acaricidal pests which have acquired resistance to 4-bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) pyrrole-3-carbonitrile in one place, the method is characterized in that it comprises applying to the site an effective amount of an insecticidal and acaricidal composition comprising as active ingredients 4-bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) pyrrole-3 -carbonitrile and one or several pyrethroid insecticidal ingredients.
The method according to claim 5, characterized in that the insecticidal and miticidal composition 0.1-5 parts by weight of the ingredient or "pyrethroid insecticidal ingredients with respect to one part by weight of 4-bromo-2- (4-chlorophenyl) - 1- (ethoxymethyl) -5- (trifluoromethyl) pyrrole-3-carbonitrile.
The method according to claim 5, characterized in that the pyrethroid insecticidal ingredient (s) are selected from the group consisting of the following (1) - (9): (1) ingredient extracted from pyrethrum containing (Z) - ( S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (IR) -trans-2, 2-dime ti 1-3- (2-methylpropyl-inyl) -cyclopropanecarboxylate (Pyrethrin I) and (Z) - (S) -2-methyl-4-oxo-3- ( penta-2, 4-dienyl) cyclopent-2-enyl (E) - (IR) -trans-3- (2-methoxycarbonylprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate (Pyrethrin II); (2) 2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether (Etofenprox); (3) (RS) -acyano-3-phenoxybenzyl (Z) - (1RS, 3RS) -3- (2-c l o r o - 3, 3, 3 - t r i f l u o r o p r o p e n i l) -2,2-dimethylcyclopropanecarboxylate (Cihalothrin); (4) (R S) - a - c i a n o - 4 - f l u or r o - 3 -f-enoxybenzyl (1RS, 3RS; 1RS, 3SR) -3- (2, 2 -di-chloro vinyl) -2,2-dimethylcyclopropanecarboxylate (Ciflutrin); (5) (RS) -a-cyano-3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2, 2-dichlorovinyl) -2, 2-dimeti lei clopropancarboxylate (Cypermethrin); (6) 2-Methylbiphenyl-3-ylmethyl (Z) - (1RS, 3RS) -3- (2-C-3, 3, 3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate ( Bifenthrin); (7) (RS) -a-cyano-3-phenoxybenzyl-2, 2,3,3-tetramethyl-cyclopropanecarboxylate (Fenpropatrine); (8) (RS) -acyano-3-phenoxybenzyl N- (2-chloro-a, a, a, a-trifluoro-p-tolyl) -D-valinate (Fluvalinate); and (9) 3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-dimethylcycloprocarboxylate (Permethrin).
8. The method according to claim 5, characterized in that the pyrethroid insecticidal ingredient (s) are selected from the group consisting of the following (1) - (9): (1) ingredient extracted from pyrethrum containing (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (IR) -t rans -2,2-dimethyl-3- (2 -methylpropyl-inyl) -cyclopropanecarboxylate (Pyrethrin I) and (Z) - (S) -2-methyl-4-oxo-3- (penta-2,4-dienyl) cyclopent-2-enyl (E) - ( IR) -trans-3- (2-methoxycarbonylprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate (Pyrethrin II); (2) 2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether (Etofenprox); (3) (RS) -acyano-3-phenoxybenzyl (Z) - (1RS, 3RS) -3- (2-c l o r o - 3, 3, 3 - t r i f l u o r o p r o p e n i l) -2,2-dimethylcyclopropanecarboxylate (Cihalothrin); (4) (RS) -α-cyano-4-fluoro-3-f-enoxybenzyl (1RS, 3RS; 1RS, 3SR) -3- (2, 2 -di-chloro vinyl) -2,2-dimethylcyclopropanecarboxylate (Ciflutrin); (5) (RS) -a-cyano-3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (Cypermethrin); (6) 2-methylbiphenyl-3-ylmethyl (Z) - (1RS, 3RS) -3- (2-chloro-3, 3, 3-t-ri fl uoroprop-1-en-yl) -2,2-dimethylcyclopropanecarboxylate (Bifenthrin); (7) (RS) -a-cyano-3-phenoxybenzyl-2, 2,3,3-tetramethyl-cyclopropanecarboxylate (Fenpropatrine); (8) (RS) -acyano-3-phenoxybenzyl N- (2-chloro-a, a, a, a-trifluoro-p-tolyl) -D-valinate (Fluvalinate); and (9) 3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (Permethrin),
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8/261866 | 1996-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA99002967A true MXPA99002967A (en) | 2000-04-24 |
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