JPWO2020188027A5 - - Google Patents
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- JPWO2020188027A5 JPWO2020188027A5 JP2021556834A JP2021556834A JPWO2020188027A5 JP WO2020188027 A5 JPWO2020188027 A5 JP WO2020188027A5 JP 2021556834 A JP2021556834 A JP 2021556834A JP 2021556834 A JP2021556834 A JP 2021556834A JP WO2020188027 A5 JPWO2020188027 A5 JP WO2020188027A5
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- alkyl
- compound according
- haloalkyl
- halogen
- cycloalkyl
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Description
以下の化合物は、500ppmの施用量で少なくとも80%の死亡率の効果をもたらした:
P1、P2、P3、P5、P6、P7、P14、P27、P28、P29。
本発明のまた別の態様は、以下のとおりであってもよい。
〔1〕式I
[化1]
(式中、
A
1
は、N又はC-R
2c
であり;
R
2c
は、H、ハロゲン、C
1
~C
3
アルキル、C
1
~C
3
ハロアルキル、C
1
~C
3
アルコキシ又はC
1
~C
3
ハロアルコキシであり;
R
2a
は、C
3
~C
6
シクロアルキル、C
1
~C
3
アルキルと、C
1
~C
3
ハロアルキルと、シアノと、ハロゲンとから独立して選択される1~3個の置換基で置換されたC
3
~C
6
シクロアルキル、C
3
~C
6
シクロアルキルC
1
~C
4
アルキル、C
1
~C
3
アルキルと、C
1
~C
3
ハロアルキルと、シアノと、ハロゲンとから独立して選択される1~5個の置換基で置換されたC
3
~C
6
シクロアルキルC
1
~C
4
アルキル、C
1
~C
5
シアノアルキル、C
3
~C
6
シクロアルコキシ、C
1
~C
4
アルキルスルホニル、C
1
~C
4
ハロアルキルスルホニル、C
1
~C
4
アルキルスルフィニル又はC
1
~C
4
ハロアルキルスルフィニルであり;
R
2b
は、H、ハロゲン、C
1
~C
3
アルキル、C
1
~C
3
ハロアルキル、C
1
~C
3
ハロアルキルチオ、C
1
~C
3
アルコキシ、C
1
~C
3
ハロアルコキシ、SF
5
又はCNであり;
A
2
は、CR
4b
又はNであり;
R
4b
は、水素又はハロゲンであり;
R
4a
は、シアノ又はC
1
~C
3
ハロアルコキシであり;
R
1
は、H、C
1
~C
6
アルキル、C
1
~C
6
シアノアルキル、アミノカルボニルC
1
~C
6
アルキル、ヒドロキシカルボニルC
1
~C
6
アルキル、C
1
~C
6
ニトロアルキル、トリメチルシランC
1
~C
6
アルキル、C
1
~C
6
ハロアルキル、C
2
~C
6
アルケニル、C
2
~C
6
ハロアルケニル、C
2
~C
6
アルキニル、C
2
~C
6
ハロアルキニル、C
3
~C
4
シクロアルキルC
1
~C
2
アルキル-、C
3
~C
4
シクロアルキルC
1
~C
2
アルキル-(ここで、前記C
3
~C
4
シクロアルキル基は、1又は2個のハロ原子で置換されている)、オキセタン-3-イル-CH
2
-、ベンジル又はハロ若しくはC
1
~C
6
ハロアルキルで置換されたベンジルであり;
R
3
は、C
1
~C
3
アルキル又はC
1
~C
3
ハロアルキルであり;
Q
1
は、Nであり、及びQ
2
は、CR
5
であり;及び
R
5
は、H、C
1
~C
3
アルキル、C
1
~C
3
ハロアルキル、C
3
~C
4
シクロアルキル、C
1
~C
3
アルコキシ又はC
1
~C
3
アルコキシカルボニルである)
の化合物又は前記式Iの化合物の農芸化学的に許容可能な塩、立体異性体、鏡像異性体、互変異性体及びN-オキシド。
〔2〕R
3
は、メチルである、前記〔1〕に記載の化合物。
〔3〕A
1
は、Nである、前記〔1〕又は〔2〕に記載の化合物。
〔4〕A
1
は、C-R
2c
であり、ここで、R
2c
は、水素又はハロゲン;好ましくは水素である、前記〔1〕又は〔2〕に記載の化合物。
〔5〕R
1
は、水素、メチル、エチル、n-プロピル、イソブチル、シクロプロピルメチル又はHCH≡CCH
2
-である、前記〔1〕~〔4〕のいずれか一項に記載の化合物。
〔6〕R
2a
は、C
3
~C
6
シクロアルキル、C
1
~C
3
アルキルと、C
1
~C
3
ハロアルキルと、シアノと、ハロゲンとから独立して選択される1~3個の置換基で置換されたC
3
~C
6
シクロアルキル、ハロゲンから独立して選択される1~5個の置換基で置換されたC
3
~C
6
シクロアルキルC
1
~C
4
アルキル、C
1
~C
5
シアノアルキル、C
3
~C
6
シクロアルコキシ、C
1
~C
4
ハロアルキルスルホニル又はC
1
~C
4
ハロアルキルスルフィニルである、前記〔1〕~〔5〕のいずれか一項に記載の化合物。
〔7〕R
2b
は、ハロゲン、C
1
~C
3
ハロアルキル、C
1
~C
3
ハロアルキルチオ、C
1
~C
3
アルコキシ、C
1
~C
3
ハロアルコキシ又はCNである、前記〔1〕~〔6〕のいずれか一項に記載の化合物。
〔8〕R
4a
は、シアノ又はC
1
~C
3
フルオロアルコキシである、前記〔1〕~〔7〕のいずれか一項に記載の化合物。
〔9〕A
2
は、Nである、前記〔1〕~〔8〕のいずれか一項に記載の化合物。
〔10〕A
2
は、CHである、前記〔1〕~〔8〕のいずれか一項に記載の化合物。
〔11〕R
5
は、水素、メチル、シクロプロピル又は2,2,2-トリフルオロエチルである、前記〔1〕~〔10〕のいずれか一項に記載の化合物。
〔12〕前記〔1〕~〔11〕のいずれか一項に記載の化合物と、1種以上の助剤及び希釈剤と、任意に1種以上の他の有効成分とを含む組成物。
〔13〕(i)昆虫、ダニ類、線虫又は軟体動物を駆除及び防除する方法であって、有害生物、有害生物の生息地又は有害生物による攻撃を受けやすい植物に、殺虫的、殺ダニ的、殺線虫的又は殺軟体動物的に有効な量の、前記〔1〕~〔11〕のいずれか一項に記載の化合物又は前記〔12〕に記載の組成物を適用するステップを含む方法;又は
(ii)昆虫、ダニ類、線虫又は軟体動物による攻撃から植物繁殖材料を保護する方法であって、前記繁殖材料又は前記繁殖材料が植えられている場所を、有効量の、前記〔1〕~〔11〕のいずれか一項に記載の化合物又は前記〔12〕に記載の組成物で処理するステップを含む方法;又は
(iii)寄生虫の防除を、それを必要としている動物内又は上で行う方法であって、有効量の、前記〔1〕~〔11〕のいずれか一項に記載の化合物又は前記〔12〕に記載の組成物を投与するステップを含む方法。
〔14〕前記〔1〕~〔11〕のいずれか一項に記載の化合物又は前記〔12〕に記載の組成物を含むか、又はそれで処理されているか、又はそれに付着されている、種子などの植物繁殖材料。
〔15〕式IIa
[化2]
(式中、R
1
、R
4
(前記A
2
及びR
4a
を含有する環に対応する)及びR
5
は、前記〔1〕、〔5〕又は〔8〕~〔11〕のいずれか一項において式Iについて定義されているとおりであり;ただし、A
2
がNである場合、R
4a
は、CN以外であり、及びA
2
がCHである場合、R
4a
は、CN又はジフルオロメトキシ以外である)
の化合物。
The following compounds produced a mortality effect of at least 80% at an application rate of 500 ppm:
P1, P2, P3, P5, P6, P7, P14, P27, P28, P29.
Another aspect of the present invention may be as follows.
[1] Formula I
[Chemical 1]
(In the formula,
A 1 is N or C—R 2c ;
R 2c is H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;
R 2a is substituted with 1 to 3 substituents independently selected from C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl , C 1 -C 3 haloalkyl , cyano and halogen ; independently selected from C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, cyano and halogen; C 3 -C 6 cycloalkyl, C 1 -C 4 alkyl , C 1 -C 5 cyanoalkyl , C 3 -C 6 cycloalkoxy , C 1 -C 4 alkylsulfonyl, substituted with 1 to 5 substituents from C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfinyl or C 1 -C 4 haloalkylsulfinyl;
R 2b is H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkylthio, C 1 -C 3 alkoxy , C 1 -C 3 haloalkoxy, SF 5 or CN; can be;
A2 is CR4b or N ;
R 4b is hydrogen or halogen;
R 4a is cyano or C 1 -C 3 haloalkoxy;
R 1 is H, C 1 -C 6 alkyl, C 1 -C 6 cyanoalkyl, aminocarbonyl C 1 -C 6 alkyl, hydroxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 nitroalkyl, trimethylsilane C 1 -C6 alkyl, C1 - C6 haloalkyl , C2 - C6 alkenyl , C2 - C6 haloalkenyl, C2 - C6 alkynyl , C2 - C6 haloalkynyl , C3 - C4 cycloalkyl C 1 -C 2 alkyl-, C 3 -C 4 cycloalkylC 1 -C 2 alkyl- (wherein said C 3 -C 4 cycloalkyl group is substituted with 1 or 2 halo atoms) , oxetan-3-yl-CH 2 -, benzyl or benzyl substituted with halo or C 1 -C 6 haloalkyl;
R 3 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
Q 1 is N and Q 2 is CR 5 ; and
R 5 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 alkoxycarbonyl)
or agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of Formula I above.
[2] The compound according to [1] above, wherein R 3 is methyl.
[3] The compound according to [1] or [2] above, wherein A 1 is N.
[4] The compound according to [1] or [2] above, wherein A 1 is C—R 2c , wherein R 2c is hydrogen or halogen; preferably hydrogen.
[5] The compound according to any one of [1] to [4] above, wherein R 1 is hydrogen, methyl, ethyl, n-propyl, isobutyl, cyclopropylmethyl or HCH≡CCH 2 —.
[6] R 2a is 1 to 3 substituents independently selected from C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, cyano and halogen; C 3 -C 6 cycloalkyl substituted with , C 3 -C 6 cycloalkyl substituted with 1 to 5 substituents independently selected from halogen, C 1 -C 4 alkyl, C 1 -C 5 The compound according to any one of the above [1] to [5], which is cyanoalkyl , C 3 -C 6 cycloalkoxy, C 1 -C 4 haloalkylsulfonyl or C 1 -C 4 haloalkylsulfinyl.
[7] R 2b is halogen, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkylthio, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy or CN in the above [1]-[6] ] The compound as described in any one of ].
[8] The compound according to any one of [1] to [7] above, wherein R 4a is cyano or C 1 -C 3 fluoroalkoxy.
[9] The compound according to any one of [1] to [8] above, wherein A 2 is N.
[10] The compound according to any one of [1] to [8] above, wherein A 2 is CH.
[11] The compound according to any one of [1] to [10] above, wherein R 5 is hydrogen, methyl, cyclopropyl or 2,2,2-trifluoroethyl.
[12] A composition comprising the compound according to any one of [1] to [11], one or more auxiliary agents and diluents, and optionally one or more other active ingredients.
[13] (i) A method of combating and controlling insects, mites, nematodes or mollusks, wherein the pest, pest habitat or plant susceptible to pest attack is treated with an insecticidal, acaricidal A nematicidally or molluscicidal effective amount of the compound according to any one of the above [1] to [11] or the step of applying the composition according to the above [12] method; or
(ii) A method of protecting plant propagation material from attack by insects, mites, nematodes or mollusks, wherein said propagation material or the site in which said propagation material is planted is protected from an effective amount of said [1] A method comprising the step of treating with the compound according to any one of [11] or the composition according to [12]; or
(iii) A method for controlling parasites in or on an animal in need thereof, comprising an effective amount of the compound according to any one of [1] to [11] or [12]. 3. A method comprising administering a composition according to .
[14] Seeds containing, treated with, or attached to the compound according to any one of [1] to [11] or the composition according to [12] plant propagation material.
[15] Formula IIa
[Chemical 2]
(wherein R 1 , R 4 ( corresponding to the ring containing A 2 and R 4a ) and R 5 are any one of [1], [5] or [8] to [11] with the proviso that when A2 is N, R4a is other than CN, and when A2 is CH, R4a is other than CN or difluoromethoxy be)
compound.
Claims (16)
A1は、N又はC-R2cであり;
R2cは、H、ハロゲン、C1~C3アルキル、C1~C3ハロアルキル、C1~C3アルコキシ又はC1~C3ハロアルコキシであり;
R2aは、C3~C6シクロアルキル、C1~C3アルキルと、C1~C3ハロアルキルと、シアノと、ハロゲンとから独立して選択される1~3個の置換基で置換されたC3~C6シクロアルキル、C3~C6シクロアルキルC1~C4アルキル、C1~C3アルキルと、C1~C3ハロアルキルと、シアノと、ハロゲンとから独立して選択される1~5個の置換基で置換されたC3~C6シクロアルキルC1~C4アルキル、C1~C5シアノアルキル、C3~C6シクロアルコキシ、C1~C4アルキルスルホニル、C1~C4ハロアルキルスルホニル、C1~C4アルキルスルフィニル又はC1~C4ハロアルキルスルフィニルであり;
R2bは、H、ハロゲン、C1~C3アルキル、C1~C3ハロアルキル、C1~C3ハロアルキルチオ、C1~C3アルコキシ、C1~C3ハロアルコキシ、SF5又はCNであり;
A2は、CR4b又はNであり;
R4bは、水素又はハロゲンであり;
R4aは、シアノ又はC1~C3ハロアルコキシであり;
R1は、H、C1~C6アルキル、C1~C6シアノアルキル、アミノカルボニルC1~C6アルキル、ヒドロキシカルボニルC1~C6アルキル、C1~C6ニトロアルキル、トリメチルシランC1~C6アルキル、C1~C6ハロアルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C2~C6アルキニル、C2~C6ハロアルキニル、C3~C4シクロアルキルC1~C2アルキル-、C3~C4シクロアルキルC1~C2アルキル-(ここで、前記C3~C4シクロアルキル基は、1又は2個のハロ原子で置換されている)、オキセタン-3-イル-CH2-、ベンジル又はハロ若しくはC1~C6ハロアルキルで置換されたベンジルであり;
R3は、C1~C3アルキル又はC1~C3ハロアルキルであり;
Q1は、Nであり、及びQ2は、CR5であり;及び
R5は、H、C1~C3アルキル、C1~C3ハロアルキル、C3~C4シクロアルキル、C1~C3アルコキシ又はC1~C3アルコキシカルボニルである)
の化合物又は前記式Iの化合物の農芸化学的に許容可能な塩、立体異性体、鏡像異性体、互変異性体及びN-オキシド。 Formula I
A 1 is N or C—R 2c ;
R 2c is H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;
R 2a is substituted with 1 to 3 substituents independently selected from C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, cyano and halogen; independently selected from C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, cyano and halogen; C 3 -C 6 cycloalkyl, C 1 -C 4 alkyl, C 1 -C 5 cyanoalkyl, C 3 -C 6 cycloalkoxy, C 1 -C 4 alkylsulfonyl, substituted with 1 to 5 substituents from C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfinyl or C 1 -C 4 haloalkylsulfinyl;
R 2b is H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkylthio, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, SF 5 or CN; can be;
A2 is CR4b or N;
R 4b is hydrogen or halogen;
R 4a is cyano or C 1 -C 3 haloalkoxy;
R 1 is H, C 1 -C 6 alkyl, C 1 -C 6 cyanoalkyl, aminocarbonyl C 1 -C 6 alkyl, hydroxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 nitroalkyl, trimethylsilane C 1 - C6 alkyl, C1 - C6 haloalkyl , C2-C6 alkenyl, C2 - C6 haloalkenyl, C2 - C6 alkynyl, C2 -C6 haloalkynyl , C3 - C4 cycloalkyl C 1 -C 2 alkyl-, C 3 -C 4 cycloalkylC 1 -C 2 alkyl- (wherein said C 3 -C 4 cycloalkyl group is substituted with 1 or 2 halo atoms) , oxetan-3-yl-CH 2 -, benzyl or benzyl substituted with halo or C 1 -C 6 haloalkyl;
R 3 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
Q 1 is N and Q 2 is CR 5 ; and R 5 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 - C 3 alkoxy or C 1 -C 3 alkoxycarbonyl)
or agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of Formula I above.
(ii)昆虫、ダニ類、線虫又は軟体動物による攻撃から植物繁殖材料を保護する方法であって、前記繁殖材料又は前記繁殖材料が植えられている場所を、有効量の、請求項1~11のいずれか一項に記載の化合物又は請求項12に記載の組成物で処理するステップを含む方法;又は
(iii)寄生虫の防除を、それを必要としている非ヒト動物内又は上で行う方法であって、有効量の、請求項1~11のいずれか一項に記載の化合物又は請求項12に記載の組成物を投与するステップを含む方法。 (i) A method of combating and controlling insects, acarids, nematodes or mollusks, wherein the pest, pest habitat or plant susceptible to pest attack is treated with an insecticidal, acaricidal or toxic agent. or (ii) an insect 12. A method of protecting plant propagation material from attack by, mites, nematodes or mollusks, wherein said propagation material or the site in which said propagation material is planted is protected from any of claims 1 to 11 in an effective amount. or (iii) a method of controlling parasites in or on a non-human animal in need thereof, wherein , an effective amount of a compound according to any one of claims 1 to 11 or a composition according to claim 12.
の化合物。 Formula IIa
compound.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19164088 | 2019-03-20 | ||
EP19164088.7 | 2019-03-20 | ||
PCT/EP2020/057593 WO2020188027A1 (en) | 2019-03-20 | 2020-03-19 | Pesticidally active azole amide compounds |
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---|---|
JP2022525967A JP2022525967A (en) | 2022-05-20 |
JPWO2020188027A5 true JPWO2020188027A5 (en) | 2023-03-27 |
Family
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---|---|
US (1) | US20220183294A1 (en) |
EP (1) | EP3941915A1 (en) |
JP (1) | JP2022525967A (en) |
CN (1) | CN113631552A (en) |
WO (1) | WO2020188027A1 (en) |
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TW202134226A (en) | 2019-11-18 | 2021-09-16 | 德商拜耳廠股份有限公司 | Novel heteroaryl-triazole compounds as pesticides |
TW202136248A (en) | 2019-11-25 | 2021-10-01 | 德商拜耳廠股份有限公司 | Novel heteroaryl-triazole compounds as pesticides |
WO2021122645A1 (en) * | 2019-12-20 | 2021-06-24 | Syngenta Crop Protection Ag | Pesticidally active azole-amide compounds |
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- 2020-03-19 US US17/441,082 patent/US20220183294A1/en active Pending
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