JPS6139943B2 - - Google Patents
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- Publication number
- JPS6139943B2 JPS6139943B2 JP2421078A JP2421078A JPS6139943B2 JP S6139943 B2 JPS6139943 B2 JP S6139943B2 JP 2421078 A JP2421078 A JP 2421078A JP 2421078 A JP2421078 A JP 2421078A JP S6139943 B2 JPS6139943 B2 JP S6139943B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- hydrogen atom
- chloropyrimidine
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 150000005718 5-chloropyrimidines Chemical class 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- -1 2-(2-methylphenoxy)-5-chloropyrimidine Chemical compound 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XSNINFUWANOXMA-UHFFFAOYSA-N 5-bromo-2-(2-chlorophenoxy)pyrimidine Chemical compound ClC1=CC=CC=C1OC1=NC=C(Br)C=N1 XSNINFUWANOXMA-UHFFFAOYSA-N 0.000 description 1
- IVBRWIXOEUXCIR-UHFFFAOYSA-N 5-bromo-2-(2-methylphenoxy)pyrimidine Chemical compound CC1=CC=CC=C1OC1=NC=C(Br)C=N1 IVBRWIXOEUXCIR-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
この発明は新規な２−フエノキシピリミジン誘
導体に関する。
アグリカルチユラル・アンド・バイオロジカ
ル・ケミストリー〔（Agr.Biol.Chem.、30、
896、（1966）〕において、式
This invention relates to novel 2-phenoxypyrimidine derivatives. Agricultural and Biological Chemistry [(Agr.Biol.Chem., 30 ,
896, (1966)], the formula
【式】を
有するフエノキシピリミジン誘導体がその除草活
性と共に記載されている。式中、R1は塩素原
子；メチルチオ基；フエニル基；メチル、メトキ
シ、塩素原子を置換分として１または２個有する
か有しないフエノキシ基を示し、R2は水素原
子；メチル基；メチル、メトキシ、塩素原子を置
換分として１または２個有するか有しないフエノ
キシ基を示す。R3は水素原子またはニトロ基を
示し、R4は水素原子またはメチル基を示してい
る。
また、フエノキシピリミジンの類似誘導体が、
式Phenoxypyrimidine derivatives having the formula are described along with their herbicidal activity. In the formula, R 1 is a chlorine atom; a methylthio group; a phenyl group; methyl, methoxy, or a phenoxy group with or without one or two chlorine atoms as a substituent; R 2 is a hydrogen atom; a methyl group; methyl, methoxy , represents a phenoxy group with or without one or two chlorine atoms as a substituent. R 3 represents a hydrogen atom or a nitro group, and R 4 represents a hydrogen atom or a methyl group. In addition, similar derivatives of phenoxypyrimidine are
formula
元素分析値（％） C15H15ON2Clとして
計算値 Ｃ、65.57；Ｈ、5.50；Ｎ、10.20；
Cl、12.90
実験値 Ｃ、65.59；Ｈ、5.60；Ｎ、10.30、；
Cl、12.78
上記実施例４の方法に準じて次の化合物が製造
された。
２−（２−アリル−６−メチルフエノキシ）−５
−クロロピリミジン、
ｎ２２ Ｄ 1.5734
２−（２−アリル−３・５−ジメチルフエノキ
シ）−５−クロロピリミジン、
ｎ２２ Ｄ 1.5721
２−（２−メチルフエノキシ）−５−クロロピリ
ミジン、
b.p. 129〜130゜／0.15mmHg
２−（２−クロロフエノキシ）−５−クロロピリ
ミジン、
b.p. 130〜132℃／0.2mmHg
２−〔２−（２−メチルプロペニル）フエノキ
シ〕−５−クロロピリミジン、
ｎ２０ Ｄ 1.5857
２−（２−アリル−４−フルオロフエノキシ）−
５−クロロピリミジン、
ｎ２１ Ｄ 1.5652
２−（４−アリル−２−メトキシフエノキシ）−
５−クロロピリミジン、
ｎ２０ Ｄ 1.5819
２−〔２−（２−ブテニル）−６−イソプロピル
フエノキシ〕−５−クロロピリミジン、
ｎ２４ Ｄ 1.5567
２−（２−アリル−４−メチルフエノキシ）−５
−クロロピリミジン、
m.p. 57〜58℃
２−（２−アリル−４−メトキシフエノキシ）−
５−クロロピリミジン、
m.p. 59〜60℃
２−（２−アリル−６−フルオロフエノキシ）−
５−クロロピリミジン、
ｎ２２ Ｄ 1.5635
２−〔２−（２−ブテニル）−４−クロロフエノ
キシ〕−５−クロロピリミジン、
ｎ１７ Ｄ 1.5808
２−（２−アリルフエノキシ）−５−ヨードピリ
ミジン、
m.p. 69〜70℃
２−（２−ｎ−プロピルフエノキシ）−５−クロ
ロピリミジン、
b.p. 119〜125℃／0.07mmHg
２−（２−アリル−４−メチルチオフエノキ
シ）−５−クロロピリミジン、
m.p. 41〜42℃
２−（４−アリル−２・６−ジクロロフエノキ
シ）−５−クロロピリミジン、
m.p. 73〜74℃
２−〔２−（２−メチルアリル）フエノキシ〕−
５−クロロピリミジン、
ｎ２２ Ｄ 1.5713
２−〔２−（１−メチルアリル）フエノキシ〕−
５−クロロピリミジン、
ｎ１７ Ｄ 1.5744
２−（２−アリル−４−クロロフエノキシ）−５
−クロロピリミジン、
m.p. 71℃
２−（３・５−ジメチルフエノキシ）−５−クロ
ロピリミジン、
b.p. 128℃／0.2mmHg
２−（２−アリル−３・５−ジメチルフエノキ
シ）−５−ブロモピリミジン、
b.p. 132〜136℃／0.1mmHg
２−〔２−（２−ブテニル）フエノキシ）−５−
ブロモピリミジン、
b.p. 136〜139℃／0.06mmHg
２−（２−クロロフエノキシ）−５−ブロモピリ
ミジン、
b.p. 135〜142℃／0.2mmHg
２−（２−アリルフエノキシ）−５−ブロモピリ
ミジン、
b.p. 150〜155℃／0.15mmHg
２−（２−メチルフエノキシ）−５−ブロモピリ
ミジン、
m.p. 71〜72℃
２−（３・５−ジクロロフエノキシ）−５−ブロ
モピリミジン、
m.p. 126〜127℃
２−（３・５−ジメチルフエノキシ）−５−ブロ
モピリミジン、
m.p. 91〜92℃
２−（２−イソプロピルフエノキシ）−５−ブロ
モピリミジン、
m.p. 60〜61℃
２−（３・５−ジメトキシフエノキシ）−５−ブ
ロモピリミジン、
m.p. 79℃
２−（２−アリル−４−メトキシフエノキシ）−
５−ブロモ−４・６−ジメチルピリミジン、
m.p. 81℃
２−（２−アリル−４−メチルフエノキシ）−５
−ブロモ−４・６−ジメチルピリミジン、
b.p. 170℃／0.3mmHg
２−（２−アリル−４−ブロモフエノキシ）−５
−ブロモ−４・６−ジメチルピリミジン、
m.p. 97〜98℃
２−（２−アリル−４−メチルチオフエノキ
シ）−５−ブロモ−４・６−ジメチルピリミジ
ン、
m.p. 72℃
２−（１−アリル−２−ナフチルオキシ）−５−
ブロモ−４・６−ジメチルピリミジン、
m.p. 112℃
２−（２−アリルフエノキシ）−５−ブロモ−
４・６−ジメチルピリミジン、
b.p. 128〜130℃／0.07mmHg
実施例 ５
２−（２−アリルフエノキシ）−５−クロロピリ
ミジン−4′−イル酢酸
実施例３で得られた２−（２−アリルフエノキ
シ）−５−クロロピリミジン−4′−イル酢酸 メ
チルエステル3.2ｇをジオキサン10mlに溶解し、
1N−水酸化ナトリウム溶液20mlを加え室温で30
分間撹拌した後、反応混合物を氷冷しながら6N
−塩酸溶液でPH＝１となし、次いで酢酸エチル
200mlで抽出した。抽出液を水50ml×２で洗滌
し、無水硫酸ナトリウムで乾燥後溶剤を減圧下に
留去し、得られた油状物にベンゼンおよびｎ−ヘ
キサン夫々20mlを加え、次いでエーテルを加えて
氷冷した白色結晶を取しｎ−ヘキサンで洗滌し
た後乾燥すると目的化合物2.5ｇが得られた。収
率82％。
m.p. 110〜112℃（無色鱗片状晶、再結溶媒；
ベンゼン−ｎ−ヘキサン）
元素分析値（％） C15H13O3N2Clとして
計算値 Ｃ、59.12；Ｈ、4.30；Ｎ、9.19；Cl、
11.63
実験値 Ｃ、59.01；Ｈ、4.28；Ｎ、9.13；Cl、
11.45。
Elemental analysis value (%) C 15 H 15 ON 2 Calculated value as Cl C, 65.57; H, 5.50; N, 10.20;
Cl, 12.90 Experimental value C, 65.59; H, 5.60; N, 10.30;
Cl, 12.78 The following compound was prepared according to the method of Example 4 above. 2-(2-allyl-6-methylphenoxy)-5
-chloropyrimidine, n 22 D 1.5734 2-(2-allyl-3,5-dimethylphenoxy)-5-chloropyrimidine, n 22 D 1.5721 2-(2-methylphenoxy)-5-chloropyrimidine, bp 129 ~ 130°/0.15mmHg 2-(2-chlorophenoxy)-5-chloropyrimidine, bp 130-132°C/0.2mmHg 2-[2-(2-methylpropenyl)phenoxy]-5-chloropyrimidine, n 20 D 1.5857 2-(2-allyl-4-fluorophenoxy)-
5-chloropyrimidine, n 21 D 1.5652 2-(4-allyl-2-methoxyphenoxy)-
5-chloropyrimidine, n 20 D 1.5819 2-[2-(2-butenyl)-6-isopropylphenoxy]-5-chloropyrimidine, n 24 D 1.5567 2-(2-allyl-4-methylphenoxy)-5
-chloropyrimidine, mp 57-58℃ 2-(2-allyl-4-methoxyphenoxy)-
5-chloropyrimidine, mp 59-60℃ 2-(2-allyl-6-fluorophenoxy)-
5-chloropyrimidine, n 22 D 1.5635 2-[2-(2-butenyl)-4-chlorophenoxy]-5-chloropyrimidine, n 17 D 1.5808 2-(2-allylphenoxy)-5-iodopyrimidine, mp 69-70℃ 2-(2-n-propylphenoxy)-5-chloropyrimidine, bp 119-125℃/0.07mmHg 2-(2-allyl-4-methylthiophenoxy)-5-chloropyrimidine, mp 41~42℃ 2-(4-allyl-2,6-dichlorophenoxy)-5-chloropyrimidine, mp 73~74℃ 2-[2-(2-methylallyl)phenoxy]-
5-chloropyrimidine, n 22 D 1.5713 2-[2-(1-methylallyl)phenoxy]-
5-chloropyrimidine, n 17 D 1.5744 2-(2-allyl-4-chlorophenoxy)-5
-chloropyrimidine, mp 71℃ 2-(3,5-dimethylphenoxy)-5-chloropyrimidine, bp 128℃/0.2mmHg 2-(2-allyl-3,5-dimethylphenoxy)-5- Bromopyrimidine, bp 132-136℃/0.1mmHg 2-[2-(2-butenyl)phenoxy)-5-
Bromopyrimidine, bp 136-139℃/0.06mmHg 2-(2-chlorophenoxy)-5-bromopyrimidine, bp 135-142℃/0.2mmHg 2-(2-allylphenoxy)-5-bromopyrimidine, bp 150- 155℃/0.15mmHg 2-(2-methylphenoxy)-5-bromopyrimidine, mp 71-72℃ 2-(3,5-dichlorophenoxy)-5-bromopyrimidine, mp 126-127℃ 2-(3・5-dimethylphenoxy)-5-bromopyrimidine, mp 91-92℃ 2-(2-isopropylphenoxy)-5-bromopyrimidine, mp 60-61℃ 2-(3,5-dimethoxyphenoxy) C)-5-bromopyrimidine, mp 79℃ 2-(2-allyl-4-methoxyphenoxy)-
5-Bromo-4,6-dimethylpyrimidine, mp 81℃ 2-(2-allyl-4-methylphenoxy)-5
-Bromo-4,6-dimethylpyrimidine, bp 170℃/0.3mmHg 2-(2-allyl-4-bromophenoxy)-5
-Bromo-4,6-dimethylpyrimidine, mp 97-98°C 2-(2-allyl-4-methylthiophenoxy)-5-bromo-4,6-dimethylpyrimidine, mp 72°C 2-(1-allyl -2-naphthyloxy)-5-
Bromo-4,6-dimethylpyrimidine, mp 112℃ 2-(2-allylphenoxy)-5-bromo-
4,6-dimethylpyrimidine, bp 128-130℃/0.07mmHg Example 5 2-(2-allylphenoxy)-5-chloropyrimidin-4'-yl acetic acid 2-(2-allylphenoxy) obtained in Example 3 Dissolve 3.2 g of -5-chloropyrimidine-4'-yl acetic acid methyl ester in 10 ml of dioxane,
Add 20ml of 1N sodium hydroxide solution and stir at room temperature for 30 minutes.
After stirring for a minute, the reaction mixture was diluted with 6N while cooling on ice.
- Adjust pH to 1 with hydrochloric acid solution, then ethyl acetate
Extracted with 200ml. The extract was washed with 2 x 50 ml of water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 20 ml each of benzene and n-hexane were added to the resulting oil, and then ether was added and cooled on ice. The white crystals were collected, washed with n-hexane, and dried to obtain 2.5 g of the target compound. Yield 82%. mp 110-112℃ (colorless scaly crystals, recrystallization solvent;
Benzene-n-hexane) Elemental analysis value (%) Calculated value as C 15 H 13 O 3 N 2 Cl C, 59.12; H, 4.30; N, 9.19; Cl,
11.63 Experimental value C, 59.01; H, 4.28; N, 9.13; Cl,
11.45.
Claims (1)
はハロゲン原子を示す。R3およびR7は同一もし
くは異なつて水素原子、１乃至６個の炭素原子を
有する低級アルキル基；３乃至５個の炭素原子を
有するアルケニル基；３または４個の炭素原子を
有するアルケニルオキシ基；５または６個の炭素
原子を有するシクロアルキル基；１乃至４個の炭
素原子を有する低級アルコキシ基；トリフルオロ
メチル基またはハロゲン原子を示す。R4、R5お
よびR6は同一もしくは異なつていてもよく、
夫々、水素原子、１乃至６個の炭素原子を有する
低級アルキル基；３乃至５個の炭素原子を有する
アルケニル基；低級アルコキシ基；３または４個
の炭素原子を有するアルケニルオキシ基；１乃至
４個の炭素原子を有するアルキルチオ基；ハロゲ
ン原子；２乃至４個の炭素原子を有する脂肪族ア
シル基；２乃至５個の炭素原子を有する低級アル
コキシカルボニル基；ニトロ基；トリフルオロメ
チル基；または基−CH2COOR8（式中、R8は水
素原子または１乃至４個の炭素原子を有する低級
アルキル基を示す。）を示す。また、R4とR5、R5
とR6とは夫々連結してそれらが結合しているベ
ンゼン環に融合するベンゼン環を形成し、全体と
してナフタレンを形成してもよい。〕で表わされ
る化合物。 ２ 式において、R1が水素原子であり、R2が
ハロゲン原子であり、R3が１乃至４個の炭素原
子を有する低級アルキル基もしくは３または４個
の炭素原子を有するアルケニル基であり、R4、
R5およびR6が水素原子であり、R7が水素原子、
１乃至４個の炭素原子を有する低級アルキル基、
３または４個の炭素原子を有するアルケニル基ま
たはハロゲン原子である特許請求の範囲第１項に
記載の化合物。 ３ 式において、R2が塩素原子または臭素原
子である特許請求の範囲第２項に記載の化合物。 ４ ２−（３−トリフルオロメチルフエノキシ）−
５−クロロピリミジンである特許請求の範囲第１
項に記載の化合物。[Claims] 1 formula [In the formula, R 1 represents a hydrogen atom or a methyl group, and R 2
indicates a halogen atom. R 3 and R 7 are the same or different and are hydrogen atom, lower alkyl group having 1 to 6 carbon atoms; alkenyl group having 3 to 5 carbon atoms; alkenyloxy group having 3 or 4 carbon atoms ; a cycloalkyl group having 5 or 6 carbon atoms; a lower alkoxy group having 1 to 4 carbon atoms; a trifluoromethyl group or a halogen atom. R 4 , R 5 and R 6 may be the same or different,
each a hydrogen atom, a lower alkyl group having 1 to 6 carbon atoms; an alkenyl group having 3 to 5 carbon atoms; a lower alkoxy group; an alkenyloxy group having 3 or 4 carbon atoms; 1 to 4 an alkylthio group having 5 carbon atoms; a halogen atom; an aliphatic acyl group having 2 to 4 carbon atoms; a lower alkoxycarbonyl group having 2 to 5 carbon atoms; a nitro group; a trifluoromethyl group; -CH 2 COOR 8 (wherein R 8 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms). Also, R 4 and R 5 , R 5
and R 6 may each be connected to form a benzene ring that is fused to the benzene ring to which they are bonded, and the whole may form naphthalene. ] A compound represented by 2 In the formula, R 1 is a hydrogen atom, R 2 is a halogen atom, R 3 is a lower alkyl group having 1 to 4 carbon atoms or an alkenyl group having 3 or 4 carbon atoms, R4 ,
R 5 and R 6 are hydrogen atoms, R 7 is a hydrogen atom,
a lower alkyl group having 1 to 4 carbon atoms,
A compound according to claim 1 which is an alkenyl group having 3 or 4 carbon atoms or a halogen atom. 3. The compound according to claim 2, wherein in the formula, R 2 is a chlorine atom or a bromine atom. 4 2-(3-trifluoromethylphenoxy)-
Claim 1 which is 5-chloropyrimidine
Compounds described in Section.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2421078A JPS54117486A (en) | 1978-03-03 | 1978-03-03 | 2-phenoxypyrimidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2421078A JPS54117486A (en) | 1978-03-03 | 1978-03-03 | 2-phenoxypyrimidine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54117486A JPS54117486A (en) | 1979-09-12 |
| JPS6139943B2 true JPS6139943B2 (en) | 1986-09-06 |
Family
ID=12131930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2421078A Granted JPS54117486A (en) | 1978-03-03 | 1978-03-03 | 2-phenoxypyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54117486A (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ188244A (en) * | 1977-09-13 | 1981-04-24 | Ici Australia Ltd | 2-substituted pyrimidines compositions growth regulating processes |
| EP0223406B1 (en) * | 1985-10-15 | 1990-08-29 | Kumiai Chemical Industry Co., Ltd. | Pyrimidine derivatives and herbicidal uses thereof |
| DE3602016A1 (en) * | 1985-12-05 | 1987-06-11 | Bayer Ag | PYRI (MI) DYL-OXY AND THIO-BENZOESIC ACID DERIVATIVES |
| JPH082883B2 (en) * | 1986-06-06 | 1996-01-17 | クミアイ化学工業株式会社 | 2-Phenoxypyrimidine derivative and herbicide |
| EP0249707B1 (en) * | 1986-06-14 | 1992-03-11 | Kumiai Chemical Industry Co., Ltd. | Picolinic acid derivatives and herbicidal compositions |
| DE3854099T2 (en) * | 1987-04-14 | 1996-04-04 | Kumiai Chemical Industry Co | 2-phenoxy-pyrimidine derivatives and herbicidal composition. |
| DE3851773T2 (en) * | 1987-04-14 | 1995-04-20 | Kumiai Chemical Industry Co | 2-phenoxypyrimidine derivatives and herbicidal compositions. |
| JPH02262565A (en) * | 1988-12-19 | 1990-10-25 | Mitsui Toatsu Chem Inc | Pyrimidine derivative, its production and herbicide containing same and herbicide composition |
| US5125957A (en) * | 1989-11-01 | 1992-06-30 | Sumitomo Chemical Company, Limited | Pyrimidine derivatives |
| US5298632A (en) * | 1990-05-15 | 1994-03-29 | Sumitomo Chemical Company, Limited | Herbicidal pyrimidine compounds, compositions containing the same and method of use |
| US5232897A (en) * | 1990-05-15 | 1993-08-03 | Sumitomo Chemical Company, Limited | Herbicidal pyrimidine compounds, compositions containing the same and method of use |
| JPH04235171A (en) * | 1990-07-26 | 1992-08-24 | Sumitomo Chem Co Ltd | Sulfohydroxamic acid derivative, production thereof and herbicide containing the same derivative as active ingredient |
| AU638840B2 (en) * | 1990-07-05 | 1993-07-08 | Sumitomo Chemical Company, Limited | Pyrimidine derivative |
| JPH04327578A (en) * | 1991-04-30 | 1992-11-17 | Mitsubishi Petrochem Co Ltd | Phenoxymethylpypimidine derivative and herbicide containing the same derivative as active component |
| JP4844779B2 (en) * | 2000-03-28 | 2011-12-28 | 株式会社林原生物化学研究所 | Phenol derivatives and their production methods and uses |
| CA2934891C (en) * | 2014-01-16 | 2023-02-28 | Nicholas Ryan DEPREZ | Pyrimidinyloxy benzene derivatives as herbicides |
| CN107250134B (en) | 2015-03-18 | 2021-04-09 | Fmc公司 | Substituted pyrimidinyloxypyridine derivatives as herbicides |
| TWI828952B (en) * | 2015-06-05 | 2024-01-11 | 美商艾佛艾姆希公司 | Pyrimidinyloxy benzene derivatives as herbicides |
| ES2883273T3 (en) | 2015-07-13 | 2021-12-07 | Fmc Corp | Aryloxypyrimidinyl ethers as herbicides |
-
1978
- 1978-03-03 JP JP2421078A patent/JPS54117486A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54117486A (en) | 1979-09-12 |
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