US 201402881 84A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0288.184 A1 Fukumoto et al. (43) Pub. Date: Sep. 25, 2014 (54) GYLOXIME DERIVATIVE AND PEST Publication Classification CONTROL AGENT (51) Int. Cl. (71) Applicants: KUMIAI CHEMICAL INDUSTRY AOIN 37/52 (2006.01) CO.,LTD., Tokyo (JP); IHARA AOIN37/18 (2006.01) CHEMICAL INDUSTRY CO.,LTD., (52) U.S. Cl. Tokyo (JP) CPC ................ A0IN37/52 (2013.01); A0IN37/18 (72) Inventors: Shunichirou Fukumoto, Shizuoka (JP); (2013.01) Daisuke Shikama, Shizuoka (JP); USPC ........... 514/626; 564/256; 564/198: 564/189: Toshihiro Nagata, Shizuoka (JP); 564/191; 514/640; 514/613 Katsuya Kato, Shizuoka (JP); Kei Kawamoto, Shizuoka (JP); Masaaki (57) ABSTRACT Komatsu, Tokyo (JP); Takeshi The present invention provides a glyoxime derivative display Matsuda, Tokyo (JP); Seisuke Ito, ing excellent pesticidal effect or a salt thereof and a pesticide Tokyo (JP) containing the same as an active ingredient. This pesticide is characterized by containing as an active ingredient, a gly (73) Assignees: IHARACHEMICAL INDUSTRY oxime derivative expressed by the general formula II (in CO.,LTD., Tokyo (JP); KUMIAI which X represents a cyano group or a carbamoyl group, R' CHEMICAL INDUSTRY CO.,LTD., represents a C-C alkyl group, a C-C cycloalkyl C-C, Tokyo (JP) alkyl group, etc., and IV represents a hydrogenatom, a C-Cs alkyl group, a C-C cycloalkyl C-C alkyl group, etc.) oran (21) Appl. No.: 14/360,527 agriculturally acceptable salt thereof. (22) PCT Filed: Nov. 19, 2012 (86). PCT No.: PCT/UP2012/007400 S371 (c)(1), N R2 (2), (4) Date: May 23, 2014 R11 O NN 2 21 no-1 (30) Foreign Application Priority Data Nov.30, 2011 (JP) ................................. 2011-261804 US 2014/0288.184 A1 Sep. 25, 2014 GYLOXIME DERVATIVE AND PEST CONTROL AGENT formula 1 TECHNICAL FIELD X 0001. The present invention relates to a novel glyoxime 2 derivative or a salt thereof, as well as to a pest control agent R -ON Na 2 N No1 R characterized by containing the derivative or salt thereofas an active ingredient. BACKGROUND ART {in the formula, 0002 For example, Patent Literature 1 is already known as X is a cyano group or a carbamoyl group, a literature regarding compounds similar to the glyoxime R" is a C-Cs alkyl group, a C-C alkenyl group, a C-C, derivative of the present invention. alkynyl group, a C-C cycloalkyl group, a C-C cycloalkyl 0003 Glyoxime derivatives are disclosed in the Patent C-C alkyl group, a C-Chaloalkyl group, a C-C alkoxy Literature 1. However, they are restricted to those glyoxime C-C alkyl group, a cyano C-C alkyl group or a phenyl derivatives in which the Substituent on one oxygen is a Sulfo C-C alkyl group which may be substituted by at least one nyl group (e.g. methanesulfonyl group), and no glyoxime substituent selected from the below-shown substituent group derivative according to the present invention is disclosed. C. and Further in the literature, there is no disclosure on the control R is a hydrogenatom, a C-Cs alkyl group, a C-C alkenyl effect of the glyoxime derivatives on pests. group, a C-C alkynyl group, a C-C cycloalkyl group, a C-C cycloalkyl C-C alkyl group, a C-C haloalkyl PRIOR ART LITERATURE group, a C-C alkoxy C-C alkyl group, a cyano C-C, alkyl group or a phenyl C-C alkyl group which may be Patent Literature substituted by at least one substituent selected from the 0004 Patent literature 1: EP-795551 below-shown Substituent group C. SUMMARY OF THE INVENTION Substituent Group C. 0010 a halogen atom, a C-C alkyl group, a C-C, Task to Be Achieved by the Invention haloalkyl group, a C-C alkoxy group, a C-Chaloalkoxy 0005. It is desired that the pest control agents used for group, a nitro group or a cyano group. useful crops are applied to Soil or foliage at a low chemical or an agriculturally acceptable salt thereof. dose and yet exhibit a sufficient pest control effect. With the increasing requirements for the safety of chemical Substances (2) A glyoxime derivative represented by the general formula and the effect on environment, it is also desired to develop a safer pest control agent. Further, in recent years, the use over many years, of pest control agents (e.g. insecticides and miti cides) have caused the appearance of pests resistant to these formula 2) pest control agents, making difficult the complete control of pests. Also, the use of highly toxic pest control agents has caused problems regarding, for example, the safety to pest control agent operator. 0006 Under such a situation, the task of the present inven tion is to solve the above-mentioned problems of conven tional pest control agents and provide a pest control agent Superior in Safety, control effect, etc. 0007 Means for Achieving the Task {in the formula, 0008. In order to develop a pest control agent having the X" is a cyano group or a carbamoyl group, above-mentioned preferred properties, the present inventors R" is a C-Cs alkyl group, a C-C alkenyl group, a C-C, synthesized various glyoxime derivatives and investigated alkynyl group, a C-C cycloalkyl group, a C-C cycloalkyl their physiological activities. As a result, it was found that the C-C alkyl group, a C-Chaloalkyl group, a C-C alkoxy glyoxime derivatives represented by the general formula I C-C alkyl group, a cyano C-C alkyl group or a phenyl shown below show a control effect to pests and resistant pests C-C alkyl group which may be substituted by at least one and show a very high control (insecticidal) effect particularly substituent selected from the below-shown substituent group to Hemipteran pests represented by Nilaparvata lugens, Lao C. and delphax striatella, Nephotettix cincticeps, Aphis gossypii, etc. I0011) R' is a hydrogen atom, a C-C alkyl group, a The finding has led to the completion of the present invention. C-C alkenyl group, a C-C alkynyl group, a C-C, 0009. The present invention has a scope characterized as cycloalkyl group, a C-C cycloalkyl C-C alkyl group, a shown below C-Chaloalkyl group, a C-C alkoxy C-C alkyl group, a (1) A pest control agent characterized by containing, as an cyano C-C alkyl group or a phenyl C-C alkyl group active ingredient, a glyoxime derivative represented by the which may be substituted by at least one substituent selected general formula II from the below-shown Substituent group C. US 2014/0288.184 A1 Sep. 25, 2014 Substituent Group C. hexyl, 4.4-dimethylpentyl, n-octyl, 1-methylheptyl, 6-meth 0012 a halogen atom, a C-C alkyl group, a C-C, ylheptyl and 5,5-dimethylhexyl groups. haloalkyl group, a C-C alkoxy group, a C-C haloalkoxy 0020. In the present invention, C-C alkenyl group refers group, a nitro group or a cyano group, to, unless otherwise specified, a straight chain or branched or an agriculturally acceptable salt thereof. chain alkenyl group of 2 to 6 carbon atoms. There can be (3) A pest control agent according to (1), which is an insec mentioned, for example, vinyl, 1-propenyl, isopropenyl, ticide. 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, (4) A method for pest control which uses the glyoxime deriva 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, tive or agriculturally acceptable salt thereof, according to (2), 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, 1-ethyl-2- at an effective amount. propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-me (5) A method for pest control according to (4), which uses the thyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl-1- glyoxime derivative or agriculturally acceptable salt thereof, butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, as an insecticide. 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2-dimethyl-1- propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pen Effect of the Invention tadienyl, 1,3-butadien-2-yl, 1-hexenyl, 1-propyl-2-propenyl, 2-hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hex 0013 The present invention shows an excellent control enyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3- effect to a variety of pests in agricultural and horticultural butenyl, 4-methyl-1-penten-2-yl, 1-ethyl-1-methyl-2-prope fields, can control even resistant pests, and are highly effec nyl, 1-ethyl-2-methyl-2-propenyl, 4-methyl-1-penten-3-yl, tive particularly to Hemipteran pests represented by Nilapar 2-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pen vata lugens, Laodelphax striatella, Sogatella fircifera, tenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, Nephotettix cincticeps, Aphis gossypii, Bemisia tabaci. etc. 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3- butenyl, 1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, MODE FOR CARRYING OUT THE INVENTION 1.5-hexadienyl, 1.4-pentadien-2-yl, and 2.4-hexadienyl 0014 Explanation is made on the symbols and terms used groups. in the present Description. 0021. In the present invention, C-C alkynyl group refers 0015. In the present invention, pest control agent means to, unless otherwise specified, a straight chain or branched insecticides, miticides, nematicides, etc. used in agricultural chain alkynyl group of 2 to 6 carbon atoms.