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Phthalamide derivative, pesticide for agricultural and horticultural applications which comprises said derivative, and method of utilizing said pesticide

A technology of phthalamide, derivatives, applied in the field of agricultural and horticultural pesticides, capable of solving problems such as damage

Inactive Publication Date: 2014-09-03
NIHON NOHYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Although various agricultural and horticultural insecticides have been developed so far, the damage caused by pests and the like in the production of agricultural and horticultural crops is still serious, and there are also pests that are resistant to conventional agents and other issues, therefore, it is expected to develop a new agricultural and horticultural insecticide

Method used

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  • Phthalamide derivative, pesticide for agricultural and horticultural applications which comprises said derivative, and method of utilizing said pesticide
  • Phthalamide derivative, pesticide for agricultural and horticultural applications which comprises said derivative, and method of utilizing said pesticide
  • Phthalamide derivative, pesticide for agricultural and horticultural applications which comprises said derivative, and method of utilizing said pesticide

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0836] Preparation method 3-1. Preparation method of Q1'

[0837] [Chemical formula 11]

[0838]

[0839] (Where W 1 , W 4 , W 5 , W 6 And W 7 Same definition as above).

[0840] For the general formula Q1'(W 1 =CF 3 ), for example, 4-heptafluoroisopropyl-1,2-phenylenediamine (Qa) described in JP 2001-122836 A can be used in accordance with J. Am. Chem. Soc., 75 Volume, (1953), page 1292, to prepare 5-heptafluoroisopropyl-2-trifluoromethyl-1H-benzimidazole.

[0841] For the general formula Q1'(W 1 =NH 2 For the compounds of ), for example, 2-amino-5-heptafluoroisopropyl-1H-benzimidazole can be prepared from Qa according to the method described in J. Chem. Soc., 1960, page 2369.

[0842] For the general formula (Q1': W 1 =EtO) derivatives, for example, in accordance with the method described in J. Heterocycl. Chem., 28, (1991), page 933, 2-ethoxy-5-heptafluoroiso can be prepared from Qa in the same manner. Propyl-1H-benzimidazole.

[0843] Preparation method 3-2. Preparation method of Q...

Embodiment 1-1

[1313] [Chemical formula 26]

[1314]

[1315] 10 g of 1,2-phenylenediamine, 32.7 g of heptafluoro-2-iodopropane, 14.6 g of sodium carbonate and 1 g of tetrabutylammonium hydrogen sulfate were sequentially added to a mixed solution of 100 ml of ethyl acetate and 100 ml of water. Under stirring at room temperature, 16 g of sodium dithionite was added in small amounts over 30 minutes. After the addition, the temperature was raised to 40°C and stirred for 1 hour. After separating the organic layer, it was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 24.3 g of 4-heptafluoroisopropyl-1,2-phenylenediamine.

[1316] 1 H-NMR(CDCl 3 ,ppm): 3.46(2H,brs), 3.61(2H,brs), 6.74(1H,d), 6.91(1H,d), 6.95(1H,s)

Embodiment 1-2

[1318] [Chemical formula 27]

[1319]

[1320] 2.76 g of 4-heptafluoroisopropyl-1,2-phenylenediamine was dissolved in 5 ml of trifluoroacetic acid, and the reaction was carried out under heating and reflux for 3 hours. After the reaction, the excess trifluoroacetic acid was distilled off under reduced pressure, and the obtained residue was washed with an ether-hexane mixed solvent to obtain 5-heptafluoroisopropyl-2-trifluoromethyl-1H-benzo Imidazole 3.1g. Physical properties: m.p.132-133°C.

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Abstract

The present invention relates to a phthalamide derivative represented by general formula (I) or a salt thereof. [In the formula, X1 represents a halogen atom or the like; X2 represents a halogen atom or the like; m represents 0, 1, 2 or 3; Y1 and Y2 independently represent a hydrogen atom, a halogen atom, an alkyl group or the like; n represents 0, 1 or 2; Z1, Z2 and Z3 may be the same as or different from one another and independently represent a nitrogen atom, CH, C-Y2 or C-A-Q (wherein at least one of Z1, Z2 and Z3 represents C-A-Q); A represents a linear or branched (C1-C8)alkylene group; Q represents a specific condensed heterocyclic group containing a nitrogen atom; R1 represents a (C1-C8)alkylthio-(C1-C8)alkyl group or the like; and R2 and R3 independently represent a hydrogen atom or the like.

Description

Technical field [0001] The present invention relates to agricultural and horticultural pesticides containing novel phthalamide derivatives or salts thereof containing fused heterocyclic groups as active ingredients and their use methods. Background technique [0002] Although various agricultural and horticultural pesticides have been developed so far, damage caused by pests, etc., in the production of agricultural and horticultural crops is still serious. In addition, there is also the emergence of pests that are resistant to conventional pesticides. and other problems, therefore, it is expected to develop a new pesticide for agriculture and horticulture. In addition, while various labor-saving application methods are being sought due to the aging of agricultural workers, the development of agricultural and horticultural insecticides having characteristics suitable for these application methods is also being sought. [0003] Patent Documents 1, 2, 3, and 4 each describe th...

Claims

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Application Information

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IPC IPC(8): C07D209/10A01N43/38A01N43/52A01N43/54A01N43/56A01N43/60A01N43/64A01N43/647A01N43/72A01N43/76A01N43/78A01N43/86A01N43/90A01P7/04A61K31/404A61K31/416A61K31/4184A61K31/4192A61K31/423A61K31/428A61K31/498A61K31/517A61K31/5415A61K31/55A61P33/14C07D209/48C07D231/56C07D235/10C07D235/26C07D239/80C07D239/91C07D239/96C07D241/44C07D249/18C07D255/04C07D263/58C07D277/68C07D279/16
CPCA01N43/90A01N43/86C07D277/68C07D235/26A01N43/54A01N43/78A01N43/56C07D235/10A01N43/647C07D263/58C07D209/10C07D279/16C07D249/18A01N43/38C07D239/91C07D209/48C07D255/04A01N43/60C07D231/56A01N43/76C07D239/96A01N43/52C07D241/44A01N43/72C07D239/80A01N43/64A01N43/84A01N47/38A61P33/14
Inventor 松崎义广中尾勇美安河内英二御所佳典远西正范诹访明之犬饲佳代中野元文藤冈伸祐三原纯
Owner NIHON NOHYAKU CO LTD
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