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United States Patent [19] [11] Patent Number: 5,872,137 Sakamoto Et Al

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United States Patent [19] [11] Patent Number: 5,872,137 Sakamoto Et Al US005872137A United States Patent [19] [11] Patent Number: 5,872,137 Sakamoto et al. [45] Date of Patent: Feb. 16, 1999 [54] DIHALOPROPENE COMPOUNDS, 4,061,683 12/1977 Karrer . INSECTICIDAL/ACARICIDAL AGENTS 4,496,440 1/1985 Campbell et al. CONTAINING SAME, AND INTERMEDIATES 4,772,633 9/1988 Matsuo et al. FOR THEIR PRODUCTION 5,302,619 4/1994 Shuto et al. 5,530,015 6/1996 Sakamoto et al. [75] Inventors: Noriyasu Sakamoto, Osaka; Masaya FOREIGN PATENT DOCUMENTS Suzuki, TakaraZuka; Kazunori Tsushima, Sanda; Kimitoshi Umeda, 0203798 12/ 1986 European Pat. Off. TakaraZuka, all of Japan 0218543 4/1987 European Pat. Off. 0227369 7/1987 European Pat. Off. [73] Assignee: Sumitomo Chemical Company, 55—120565 9/1980 Japan . 56—029504 3/1981 Japan . Limited, Osaka, Japan 1420171 1/1976 United Kingdom . 1424211 2/1976 United Kingdom . [21] Appl. No.: 917,372 1578412 11/1980 United Kingdom . [22] Filed: Aug. 26, 1997 OTHER PUBLICATIONS Related US. Application Data Head et al., J. Chem. Soc. (C), pp. 871—874 (1971). Dorman, J. Org. Chem., vol. 31, pp.3666—3671 (1966). [63] Continuation of Ser. No. 624,488, ?led as PCT/JP95/01439 English language abstract of Japanese Patent No. Jul. 20, 1995, abandoned. 55—120565 Aug. 3, 1979. [30] Foreign Application Priority Data English language abstract of Japanese Patent No. 56—029504 Aug. 16, 1979. Aug. 4, 1994 [JP] Japan .................................. .. 6-183461 Oct. 7, 1994 [JP] Japan .. 6-243931 Primary Examiner—Gary Geist Apr. 14, 1995 [JP] Japan .................................. .. 7-089737 Assistant Examiner—Sreeni Padmanabhan [51] Int. Cl.6 ................................................... .. A01N 43/40 Attorney, Agent, or Firm—Birch, SteWart, Kolasch & Birch, LLP [52] US. Cl. ........................ .. 514/345; 568/649; 568/674; 424/406 [57] ABSTRACT [58] Field of Search ................................... .. 568/649, 674; 424/406; 514/345 The dihalopropene compounds of the general formula [I] have excellent insecticidal/acaricidal activity, so that they [56] References Cited are satisfactorily effective for the control of noxious insects, mites and ticks. U.S. PATENT DOCUMENTS 4,048,235 9/1977 Karrer. 92 Claims, No Drawings 5,872,137 1 2 DIHALOPROPENE COMPOUNDS, -continued INSECTICIDAL/ACARICIDAL AGENTS R10 IIU Q3 CONTAINING SAME, AND INTERMEDIATES CH, FOR THEIR PRODUCTION (R9)l R11 P This application is a continuation of application Ser. No. Q4 08/624,488 ?led on Apr. 4, 1996, noW abandoned. This is the US. National stage Application of PCT/JP95/ 01439 ?led Jul. 20, 1995 noW WO96/04228 published Feb. (R4)m 10 15, 1996. 1. Technical Field The present invention relates to dihalopropene compounds, insecticidal/acaricidal agents containing these Q5 compounds as active ingredients, for their production. 15 2. Background Art As disclosed in JP-A 48-86835/1973 and JP-A 49-1526/ (R9) 0 1974, for example, it is Well knoWn that some kinds of propene compounds can be used as an active ingredient of R15 R10 IIU Q6 insecticides. A CH In vieW of their insecticidal/acaricidal activity, it cannot (R9)! R16 S Rn p alWays be said that these compounds are satisfactorily active for the control of noXious insects, mites and ticks. R15 R F R10 IIU Q7 Disclosure of Invention 25 0 Z1 c—o — CH, (R9)l R16 S h R11 P The present inventors have intensively studied to ?nd a compound having excellent insecticidal/acaricidal activity. R5 0 R10 R7 Q8 As a result, they have found that particular dihalopropene compounds have satisfactory insecticidal/acaricidal activity (R4)l ®i3=c(rr6)—d:—o {11 P (IIH for the control of noXious insects, mites and ticks, thereby completing the present invention. R15 IFS R10 IIU Q9 That is, the present invention provides a dihalopropene 0 A c =C(R6) CH, compound (hereinafter referred to as the present compound) (R9)! R16 S Rn p of the general formula: 35 QlU R2 [1] (R14)r Wherein R4 and R12 are independently halogen, C1—C4 alkyl, Wherein R1 is C1—C1O alkyl, C1—C5 haloalkyl, C2—C1O C1—C3 haloalkyl, C1—C3 alkoXy or C1—C3 haloalkoXy, alkenyl, C2—C6 haloalkenyl, C3—C9 alkynyl, C3—C5 45 R5 and R6 are independently hydrogen, C1—C3 alkyl, haloalkynyl, C2—C7 alkoXyalkyl, (C1—C3) alkoXy (C1—C7) tri?uoromethyl or halogen, carbonylalkyl, C2—C7 alkylthioalkyl; C3—C6 cycloalkyl R7 is hydrogen or C1—C3 alkyl, Which may be substituted With C1—C4 alkyl, C1—C3 alkoXy or C1—C3 haloalkoXy; C4—C9 cycloalkylalkyl Which may be R8 is hydrogen, halogen or methyl, substituted With C1—C4 alkyl; C5—C6 cycloalkenyl Which R9 is halogen, cyano, nitro, hydroXy, penta?uorosulfanyl may be substituted With C1—C4 alkyl; C6—C8 cycloalkeny (FSS), C1—C8 alkyl, C1—C3 haloalkyl, C1—C8 alkoXy, lalkyl Which may be substituted With C1—C4 alkyl; or Q1, Q2, haloalkoXy, C1—C3 alkylthio, C1—C3 haloalkylthio, Q3, Q4, Q5, Q6, Q7, Q8, Q9 or Q1O of the general formula: C3—C6 alkenyloXy, C3—C6 haloalkenyloXy, C1—C3 hydroXyalkyl, C2—C4 alkenyl, C2—C4 haloalkenyl, 55 C2—C4 alkynyl, C2—C4 alkynyloXy, C2—C4 haloalkynyl, IFS R10 IIU Q1 C2—C4 haloalkynyloXy, C2—C4 alkoXyalkyl, C2—C4 c =C(R6) CH, alkylthioalkyl, C3—C6 cycloalkyl, C5—C6 cycloalkenyl, 11 (R4)! R P C2—C5 alkoXycarbonyl, C3—C6 cycloalkyloXy, C5—C6 cycloalkenyloXy; phenyl Which may be substituted R10 IIU Q2 With halogen, C1—C4 alkyl, C1—C3 haloalkyl, C1—C3 CH alkoXy, C1—C3 haloalkoXy, C3—C6 alkenyloXy or C3—C6 haloalkenyloXy; phenoXy Which may be substituted (Rom R11 With halogen, C1—C4 alkyl, C1—C3 haloalkyl, C1—C3 alkoXy, C1—C3 haloalkoXy, C3—C6 alkenyloXy or C3—C6 R8 65 haloalkenyloXy; benZyl Which may be substituted With halogen, C1—C4 alkyl, C1—C3 haloalkyl, C1—C3 alkoXy, C1—C3 haloalkoXy, C3—C6 alkenyloXy or C3—C6 5,872,137 3 haloalkenyloxy; benZyloxy Which may be substituted a compound of the general formula: With halogen, C1—C4 alkyl, C1—C3 haloalkyl, C1—C3 alkoxy, C1—C3 haloalkoxy, C3—C6 alkenyloxy or C3—C6 R2 [III] haloalkenyloxy; or pyridyloxy Which may be substi tuted With halogen, C1—C4 alkyl, C1—C3 haloalkyl, HO OCH2CH=CX2 C1—C3 alkoxy, C1—C3 haloalkoxy, C3—C6 alkenyloxy or C3—C6 haloalkenyloxy; or R3 When 1 is an integer of 2 to 5, tWo adjacent Rg’s are taken together to form trimethylene, tetramethylene, methyl Wherein R2 and R3 are independently halogen, C1—C3 alkyl enedioxy Which may be substituted With halogen or or C1—C3 haloalkyl, and X’s are independently chlorine or C1—C3 alkyl; or ethylenedioxy Which may be substi bromine; tuted With halogen or C1—C3 alkyl, a compound of the general formula: R10, R11, R15 and R16 are independently hydrogen, C1—C3 15 R21 [IV] alkyl or tri?uoromethyl, A is oxygen, 5(0),, NR13, C(=G1)G2 or G1C(=G2) (CH2), —c—o OH Wherein G1 and G2 are independently oxygen or sulfur, H R13 is hydrogen, acetyl or C1—C3 alkyl, and t is an (R19)l 2 integer of 0 to 2, R22 Z1 is oxygen, sulfur or NR17 Wherein R17 is hydrogen, Wherein R21 and R22 are independently halogen or C1—C3 acetyl or C1—C3 alkyl, alkyl, R19 is halogen, C1—C3 haloalkoxy or tri?uoromethyl, u is 1 to 4, and l is an integer of 0 to 5; 1 is an integer of 0 to 5, a compound of the general formula: m is an integer of 0 to 4, R2 [V] n is an integer of 1 or 2, p is an integer of 0 to 6, R10 IIU q is an integer of 0 to 3, and Q B CH—O OH (R20)l R11 6 s is an integer of 1 to 6, R3 R2, R3 and R14 are independently halogen, C1—C3 haloalkyl or C1—C3 alkyl, Wherein R2 and R3 are independently halogen, C1—C3 alkyl or C1—C3 haloalkyl, R7 is hydrogen or C1—C3 alkyl, R10 and r is an integer of 0 to 2, R11 are independently hydrogen, C1—C3 alkyl or X’s are independently chlorine or bromine, tri?uoromethyl, R20 is halogen, C1—C3 alkoxy, tri?uorom ethyl or C1—C3 haloalkoxy, l is an integer of 0 to 5, and e is Y is oxygen, NH or sulfur, and an integer of 1 to 4; and particularly, a compound Wherein Z is oxygen, sulfur or NR13 Wherein R13 is hydrogen, B is oxygen; a compound Wherein R2 and R3 are indepen acetyl or C1—C3 alkyl. dently halogen or C1—C3 alkyl, R7, R10 and R11 are all The present invention also provides an insecticidal/ hydrogen, e is 1 to 4, and B is oxygen, 5(0); or NR13 acaricidal agent containing the above dihalopropene com Wherein R13 is hydrogen, acetyl or C1—C3 alkyl, and t is an integer of 0 to 2. pound as an active ingredient. 45 The present invention further provides the folloWing DETAILED DESCRIPTION OF THE compounds Which are useful as intermediates for producing INVENTION some of the present compounds: The variables in the above formulae for the present a compound of the general formula: compounds and their intermediates can take the folloWing speci?c examples. R2 [II] Examples of the halogen atom represented by R2, R3, R4, R5, R6, R8, R9 or R12 or present in R9 are ?uorine, chlorine, bromine or iodine. Examples of the C1—C1O alkyl group represented by R1 are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert pentyl, n-hexyl, n-heptyl, isohexyl, n-octyl, n-nonyl, n-decyl, 3-n-pentyl, 2-ethylbutyl, 1-methylpentyl, Wherein R2 and R3 are independently halogen, C1—C3 alkyl a O 1-ethylbutyl, 3-methylpentyl, 1,3-dimethylbutyl, or C1—C3 haloalkyl, R7 is hydrogen or C1—C3 alkyl, R10 and 1-methylheptyl and 1-methyloctyl.
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